Category: 221874-51-7

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.221874-51-7,(R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate,as a common compound, the synthetic route is as follows.

In a 1 L sealed tube, to a solution of (R)-tert-butyl (2-oxopiperidin-3-yl)carbamate (23 g, 110 mmol) in 1,4-dioxane (300 mL) was added 1,4-dibromobenzene (28 g, 120 mmol), potassium phosphate tribasic (34 g, 160 mmol), cuprous iodide (8.2 g, 43 mmol), Nu,Nu’- dimethylethylenediamine (4.7 ml, 43 mmol). The reaction mixture was purged with Argon for 10-15 minutes and then heated to 60 C for overnight. The reaction mixture was diluted with ethyl acetate (250 mL) and washed with brine solution (200 mL). The organic layer was dried over Na2S04 and concentrated to produce the crude product. The crude compound was purified through 330 g Silica column and was eluted with ethylacetate:pet-ether (40:60) to achieve off white solids of tert-butyl (l-(4- bromophenyl)-2-oxopiperidin-3-yl)carbamate (20 g). Chiral SFC analysis of the purified product showed -10% epimerization. The compound was then purified via SFC to afford Intermediate 1 (15 g, 40 mmol, 38% yield) as a white solid. MS(ESI) m/z: 369.0/371.0 (M+H). NMR (400 MHz, CDCh):? ppm 7.48 (d, J = 4.8 Hz, 2H), 7.11 (d, J= 4.8 Hz, 2H), 5.48 (br-s, 1H), 4.25-4.18 (m, 1H), 3.70-3.62 (m, 2H), 2.60-2.52 (m, 1H), 2.08- 1.95 (m, 2H), 1.74-1.64 (m, 1H), 1.43 (s, 9H). [a]D25 (c = 0.1, MeOH): +30.0. Chiral Purity (SFC): 99.9%, retention time = 4.15 min (time of Peak-01 (0.105%) = 3.03 min & Retention time of Peak-02 (99.9%) = 4.15 min; Co-Solvent: 0.2%DEA in Methanol; Column: Whelk-01 ( R,R )(250 X 4.6)mm 5u; Column Temperature: 24.5; Total Flow: 3; C02 Flow Rate: 1.8; Co-Solvent Flow Rate: 1.2; Co-Solvent% 40; Back Pressure 100.) (0145) Preparative SFC Conditions: Column/dimensions: Whelk(R,R) (250 X 30) mm, 5u; C02%: 70%; Co-solvent%: 30% of (0.2% DEA in methanol); Total Flow: 120 g /min; Back Pressure: 100 bar; Temperature: 30C; UV: 240 nm. Retention time of Peak-01 = 3.20 min & Retention time of Peak-02 = 4.60 min., 221874-51-7

The synthetic route of 221874-51-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHIRUDE, Pravin Sudhakar; CHATTOPADHYAY, Amit Kumar; RACHAMREDDY, Chandrasekhar; WURTZ, Nicholas R.; KICK, Ellen K.; (117 pag.)WO2018/227058; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.221874-51-7,(R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Preparation of Compound 148Step 1:(S)-tert-Butyl (l-ethyl-2-oxopiperidin-3-yl)carbamate. (S)-tert-bvAy (2-oxopiperidin- 3-yl)carbamate (1 g, 4.67 mmol) was dissolved in THF (10 mL) and the solution cooled to 0C. A 1M solution of LiHMDS (5.4 mL) in THF was added and the mixture stirred for 1 h. Iodoethane (410 iL, 5.1 mmol) was added and the reaction removed from the cooling bath and allowed to warm to room temperature and stirred overnight. The reaction was quenched with saturated aqueous NH4C1 (8 vol) and extracted with EtOAc (2 x 4 vol). The combined extracts were washed with brine, dried, filtered and evaporated. The desired product was isolated by silica gel chromatography to afford tert-butyl N- [(3S)-l-ethyl-2-oxo-3-piperidyl]carbamate. Yield: (190 mg, 16.8%). MS: m/z (obs.) 507.0 [M+H]+. IH NMR (400 MHz, CDC13) delta 6.86 (d, J = 7.8 Hz, IH), 3.85 (s, IH), 3.30 – 3.15 (m, 5H), 1.84 (ddd, J = 26.1, 16.9, 12.3 Hz, 5H), 1.38 (s, 10H), 1.01 (t, J = 7.1 Hz, 3H).

221874-51-7, As the paragraph descriping shows that 221874-51-7 is playing an increasingly important role.

Reference：
Patent; VERTEX PHARMACEUTICALS INCORPORATED; GREEN, Jeremy; WILSON, Dean, M.; KONG, Laval, Chan Chun; DAS, Sanjoy, Kumar; POISSON, Carl; COURT, John, J.; TANG, Qing; LI, Pan; COLLIER, Philip, N.; WAAL, Nathan; LAUFFER, David, J.; DORSCH, Warren; WO2012/6055; (2012); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

221874-51-7, (R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 1 L sealed tube, to a solution of (i?)-tert-butyl (2-oxopiperidin-3-yl)carbamate (23 g, 110 mmol) in 1,4-dioxane (300 mL) was added 1,4-dibromobenzene (28 g, 120 mmol), potassium phosphate tribasic (34 g, 160 mmol), cuprous iodide (8.2 g, 43 mmol), Nu,Nu’- dimethylethylenediamine (4.7 ml, 43 mmol). The reaction mixture was purged with Argon for 10-15 minutes and then heated to 60 C for overnight. The reaction mixture was diluted with ethyl acetate (250 mL) and washed with brine solution (200 mL). The organic layer was dried over Na2S04 and concentrated to produce the crude product. The crude compound was purified through 330 gm Silica column and was eluted with ethylacetate:pet-ether (40:60) to achieve off white solids of tert-butyl (l-(4- bromophenyl)-2-oxopiperidin-3-yl)carbamate (20 gm). Chiral SFC analysis of the purified product showed -10% epimerization. The compound was then purified via SFC to afford Intermeidate la (15 gm, 40 mmol, 38% yield) as a white solid. MS(ESI) m/z: 369.0/371.0 (M+H). NMR (400 MHz, CDCh): delta ppm 7.48 (d, J= 4.8 Hz, 2H), 7.11 (d, J= 4.8 Hz, 2H), 5.48 (br-s, 1H), 4.25-4.18 (m, 1H), 3.70-3.62 (m, 2H), 2.60-2.52 (m, 1H), 2.08-1.95 (m, 2H), 1.74-1.64 (m, 1H), 1.43 (s, 9H). [a]D25 (c = 0.1, MeOH): +30.0. Chiral Purity (SFC): 99.9%, retention time = 4.15 min (time of Peak-01 (0.105%) = 3.03 min & Retention time of Peak-02 (99.9%) = 4.15 min; Co-Solvent: 0.2%DEA in (0236) Methanol; Column: Whelk-01 ( R,R )(250 X 4.6)mm 5u; Column Temperature: 24.5; Total Flow: 3; C02 Flow Rate: 1.8; Co-Solvent Flow Rate: 1.2; Co-Solvent% 40; Back Pressure 100.) (0237) Preparative SFC Conditions: Column/dimensions: Whelk(R,R) (250 X 30) mm, 5u; (0238) C02%: 70%; Co-solvent%: 30% of (0.2% DEA in methanol); Total Flow: 120 g /min; Back Pressure: 100 bar; Temperature: 30C; UV: 240 nm. Retention time of Peak-01 = 3.20 min & Retention time of Peak-02 = 4.60 min;, 221874-51-7

221874-51-7 (R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate 45092193, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; WURTZ, Nicholas R.; SHIRUDE, Pravin Sudhakar; VIET, Andrew Quoc; (144 pag.)WO2018/227065; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.221874-51-7,(R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate,as a common compound, the synthetic route is as follows.

2-oxo-piperidin-3-yl carbamate (R)-tert-butyl (642 mg, 3.00 mmol) N, sodium hydride at room temperature to N- dimethylformamide (3 mL) solution of (132mg, 3.3 mmol) It was added. The reaction mixture was stirred for 30 minutes, iodomethane (206muL, 3.3 mmol) was added and stirring was continued for 1 hour. The reaction mixture was poured into water (50 mL), using the continuous extraction apparatus overnight, and extracted with EtOAc (100mL). The organic extract was evaporated to dryness under vacuum, the residue of the crude SiO2 chromatography (23g, CH2Cl2 / MeOH / NH4OH, 100: 0: 0 ~ 94: 5.7: 0.3) was purified by on, to give 1-methyl-2-oxo-piperidin-3-yl carbamic acid (R) -tert- butyl 310mg (45%) as a viscous oil colorless., 221874-51-7

221874-51-7 (R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate 45092193, apiperidines compound, is more and more widely used in various fields.

Reference：
Patent; F.HOFFMANN-LA ROCHE AG; HENDRICKS, ROBERT THAN; HERMANN, JOHANNES CORNELIUS; KONDRU, RAMA K; LOU, YAN; LYNCH, STEPHEN M; OWENS, TIMOTHY D; SOTH, MICHAEL; (50 pag.)JP5667692; (2015); B2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.221874-51-7,(R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Cuprous iodide (3.6 g, 18 mmol) was added to a mixture of tert-butyl (R)-(2- oxopiperidin-3-yl)carbamate (10 g, 47 mmol), 4-bromo-2-fluoro-l-iodobenzene (14 g, 47 mmol), and potassium phosphate tribasic (15 g, 70 mmol) in dioxane (100 mL), and the mixture was purged with nitrogen for 20 minutes. N^V-dimethylethylenediamine (2.0 mL, 18.7 mmol) was added, and the reaction mixture was stirred at 90 C overnight. The reaction mixture was filtered through celite, washed with ethyl acetate and concentrated in vacuo. The crude product was purified by column chromatography (30% ethyl acetate in pet ether). The mixture was further purified by SFC to give tert- butyl (i?)-(l-(4-bromo- 2-fluorophenyl)-2-oxopiperidin-3-yl)carbamate (3.0 g, 7.8 mmol, 17 % yield) and tert- butyl (i?)-(l-(3-fluoro-4-iodophenyl)-2-oxopiperidin-3-yl)carbamate (1.8 g, 4.1 mmol, 8.8 % yield). Analytical data for Intermediate 2: NMR (300 MHz, CDCh):? ppm 7.30 – 7.37 (m, 2H), 7.10 – 7.18 (m, 1H), 5.46 (s, 1H), 4.27 (m, 1H), 3.53 – 3.68 (m, 2H), 2.54 – 2.66 (m, 1H), 2.01 – 2.12 (m, 2H), 1.46 (s, 9H) ; 19FNMR: -117, MS(ESI) m/z: (0151) 387.2/389.2 (M+H)+. Analytical data for Intermediate 3: NMR (300 MHz, CDCh-d) ? ppm 7.49 – 7.00 (m, 2H), 6.92 – 7.00 (m, 1H), 5.46 (s, 1H), 4.27 (dt, J=11.71, 6.00Hz, 1H), 3.54 – 3.68 (m, 2H), 2.54 -2.66 (m, 1H), 2.01 – 2.12 (m, 2H), 1.74(m, 1H), 1.46 (s, 9H) ; 19F NMR: -117, MS(ESI) m/z: 435.0 (M+H)+.

221874-51-7, As the paragraph descriping shows that 221874-51-7 is playing an increasingly important role.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHIRUDE, Pravin Sudhakar; CHATTOPADHYAY, Amit Kumar; RACHAMREDDY, Chandrasekhar; WURTZ, Nicholas R.; KICK, Ellen K.; (117 pag.)WO2018/227058; (2018); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

221874-51-7, (R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 1 L sealed tube, to a solution of (R)-tert-butyl (2-oxopiperidin-3-yl)carbamate (23 g, 110 mmol) in 1,4-dioxane (300 mL) was added 1,4-dibromobenzene (28 g, 120 mmol), potassium phosphate tribasic (34 g, 160 mmol), cuprous iodide (8.2 g, 43 mmol), Nu,Nu’- dimethylethylenediamine (4.7 ml, 43 mmol). The reaction mixture was purged with Argon for 10-15 minutes and then heated to 60 C for overnight. The reaction mixture was diluted with ethyl acetate (250 mL) and washed with brine solution (200 mL). The organic layer was dried over Na2S04 and concentrated to produce the crude product. The crude compound was purified through 330 gm Silica column and was eluted with ethylacetate:pet-ether (40:60) to achieve off white solids of tert-butyl (l-(4- bromophenyl)-2-oxopiperidin-3-yl)carbamate (20 gm). Chiral SFC analysis of the purified product showed -10% epimerization. The compound was then purified via SFC to afford Intermeidate la (15 gm, 40 mmol, 38% yield) as a white solid. MS(ESI) m/z: 369.0/371.0 (M+H). NMR (400 MHz, CDCh): delta ppm 7.48 (d, J = 4.8 Hz, 2H), 7.11 (d, J= 4.8 Hz, 2H), 5.48 (br-s, 1H), 4.25-4.18 (m, 1H), 3.70-3.62 (m, 2H), 2.60-2.52 (m, 1H), 2.08-1.95 (m, 2H), 1.74-1.64 (m, 1H), 1.43 (s, 9H). [a]D25 (c = 0.1, MeOH): +30.0. Chiral Purity (SFC): 99.9%, retention time = 4.15 min (time of Peak-01 (0.105%) = 3.03 min & Retention time of Peak-02 (99.9%) = 4.15 min; Co-Solvent: 0.2%DEA in Methanol; Column: Whelk-01 ( R,R )(250 X 4.6)mm 5u; Column Temperature: 24.5; Total Flow: 3; C02 Flow Rate: 1.8; Co-Solvent Flow Rate: 1.2; Co-Solvent% 40; Back Pressure 100.) Preparative SFC Conditions: Column/dimensions: Whelk(R,R) (250 X 30) mm, 5u; C02%: 70%; Co-solvent%: 30% of (0.2% DEA in methanol); Total Flow: 120 g /min; Back Pressure: 100 bar; Temperature: 30C; UV: 240 nm. Retention time of Peak-01 = 3.20 min & Retention time of Peak-02 = 4.60 min;, 221874-51-7

As the paragraph descriping shows that 221874-51-7 is playing an increasingly important role.

Reference：
Patent; BRISTOL-MYERS SQUIBB COMPANY; WURTZ, Nicholas R.; SHIRUDE, Pravin Sudhaker; (113 pag.)WO2017/100390; (2017); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem

221874-51-7, (R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

221874-51-7, Preparation of Compound 149Step 1:(S)-tert-Butyl (l-isopropyl-2-oxopiperidin-3-yl)carbamate. (5)-tert-butyl (2- oxopiperidin-3-yl)carbamate (1.21 g, 5.69 mmol) was dissolved in DMSO (12 mL). KOH (415 mg, 7.39 mmol) was added, followed by 2-iodopropane (740 mu,, 7.4 mmol) and the mixture stirred for 72 h. The reaction was quenched by addition of saturated aqueous NH4CI (8 vol) and extracted with EtOAc (2 x 4 vol). The combined extracts were washed with brine, dried, filtered and evaporated. The desired product was isolated by silica gel chromatography to afford tert-butyl N-[(3S)-l-isopropyl-2-oxo-3-piperidyl]carbamate. Yield: (430 mg, 29.5%). MS: m/z (obs.) 279.1 [M+Na . 1H NMR (400 MHz, d6- DMSO) delta 6.83 (d, J = 8.1 Hz, 1H), 4.68 – 4.52 (m, 1H), 3.88 (d, J = 6.8 Hz, 1H), 3.12 (dd, J = 13.0, 7.2 Hz, 2H), 1.98 – 1.85 (m, 1H), 1.75 (dd, J = 12.3, 6.8 Hz, 2H), 1.56 (d, J = 17.8 Hz, 1H), 1.38 (s, 11H), 1.03 (dd, J = 6.7, 2.0 Hz, 7H).

The synthetic route of 221874-51-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; VERTEX PHARMACEUTICALS INCORPORATED; GREEN, Jeremy; WILSON, Dean, M.; KONG, Laval, Chan Chun; DAS, Sanjoy, Kumar; POISSON, Carl; COURT, John, J.; TANG, Qing; LI, Pan; COLLIER, Philip, N.; WAAL, Nathan; LAUFFER, David, J.; DORSCH, Warren; WO2012/6055; (2012); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem