Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0) belongs to piperidine derivatives.Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.HPLC of Formula: 30727-21-0
Preparation of Δ1-pyrroline-2-carboxylic acid and a new proline synthesis was written by Hasse, Kurt;Wieland, Alfred. And the article was included in Chemische Berichte in 1960.HPLC of Formula: 30727-21-0 The following contents are mentioned in the article:
2,3-Dioxopiperidine-4-carboxylic acid Et ester (I), obtained by condensation of 2-pyrrolidone (II) with (CO2Et)2 (III), was converted by hydrolysis to H2N(CH2)3COCO2H.HCl (IV) and this hydrogenated to yield DL-proline (V). K (10 g.) dissolved in 100 cc. absolute EtOH, the solution evaporated in vacuo, the residue dissolved in 200 cc. Et2O, the solution treated with 25 cc. II and 50 cc. III in 50 cc. Et2O, the mixture treated after 24 hrs. with 100 cc. 1:4 HCl, and the Et2O phase concentrated gave 90% [EtO2C(CH2)3NHCO]2 (VI), m. 106° (H2O or EtOH). VI (1 g.) in 5 cc. 6N HCl heated 1 hr. at 80° and concentrated gave [HO2C(CH2)3NHCO]2, m. 210°. II condensed in the usual manner with III, the mixture acidified with HCl, and the Et2O phase evaporated in vacuo at 120° gave 3-ethoxalyl-2-pyrrolidone (VII), m. 132° (EtOH). 3-Oxalyl-2-pyrrolidone (VIII) (0.75 g.) and 20 cc. alc. HCl kept 36 hrs. at room temperature and evaporated in vacuo yielded VII, m. 131-2° (C6H6). VII (0.5 g.) in 5 cc. 6N HCl heated 0.5 hr. at 80° gave VIII, decomposing above 205°. K (4 g.) under 60 cc. Et2O treated during 1 hr. with 13.8 g. absolute EtOH, warmed 3-4 hrs. on the water bath, treated at 0-5° with stirring with 14.6 g. III, the mixture treated after 10 min. during 0.5 hr. with 18.9 g. N-benzoyl-2-pyrrolidone in 27 cc. dry dioxane, diluted after 1 hr. with 150 cc. Et2O, and filtered after 12 hrs., the residue dried in vacuo (23 g.), added with stirring to 40 cc. H2O, 15 cc. HCl, and 30 cc. CHCl3, the CHCl3 phase evaporated, the residual oil dissolved at 90° with stirring during 10 min. in 40 cc. 6N HCl, and the hot solution filtered and cooled gave 2 g. VIII, needles, decomposing above 205° with sintering; the mother liquor gave 5.6 g. HO2CCONH(CH2)3CO2H, m. 163-4° (decomposition) (H2O or Me2CO). VIII (20.4 mg.) in 10 cc. H2O treated with 15 cc. 1% 2,4-(O2N)2C6H3NHNH2 in 2N HCl gave the 2,4-dinitrophenylhydrazone of VIII, m. 221° (decomposition). K (20 g.), a few crystals of iodine and a small amount of Hg2Cl2 in 50 cc. absolute C6H6 treated with 40 cc. absolute EtOH in portions, the mixture diluted with 30 cc. EtOH in 150 cc. C6H6, warmed slightly, diluted further with 300 cc. C6H6, treated with 43 g. II and 73 g. III, refluxed 18 hrs. with stirring, and treated with 80 cc. 6N HCl, the hot C6H6 layer decanted, the aqueous phase extracted with C6H6, and the combined C6H6 solutions worked up yielded 80% I, m. 148°. I (370 mg.) in EtOH hydrogenated at 20°/760 mm. over PtO2, filtered, and evaporated gave 3-hydroxy-4-carbethoxy-2-piperidone, m. 121-2° (C6H6). I (5.3 g.) and 80 cc. 6N HCl refluxed 6 min. (in larger runs 20 min.) and evaporated at 35°/12 mm., and the residue refrigerated several hrs., filtered, washed with cold HCl, and dried yielded IV, m. 113° (HCl-AcOH-Et2O). VIII (1.03 g.) and 35 cc. 6N HCl refluxed 1 hr. and evaporated at 35°/16 mm., the residue dissolved in H2O and chromatographed on Dowex 50-X-8 (H form), and the fractions from 207-358 cc. evaporated gave 0.7 g. IV, m. 113° (decomposition). IV (48.7 mg.) hydrogenated 3 hrs. at 21°/755 mm. over PtO2, filtered, treated with Ag2O and then H2S, refiltered, and evaporated, and the residue and 48 mg. picric acid dissolved in hot glacial AcOH and diluted with Et2O gave the picrate of V, m. 134-5°. I (12.5 g.) and 200 cc. 6N HCl refluxed 7 min., concentrated at 40°/25 mm. to 30 cc., diluted with 120 cc. H2O, hydrogenated 5 hrs. at 25°/1 atm. over 270 mg. PtO2, filtered, placed on Amberlite IR-4B, washed with 1.3 l. H2O, and eluted gave 5.51 g. pure V. This study involved multiple reactions and reactants, such as Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0HPLC of Formula: 30727-21-0).
Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0) belongs to piperidine derivatives.Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.HPLC of Formula: 30727-21-0
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem