With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1174020-40-6,(3S,4R)-tert-Butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate,as a common compound, the synthetic route is as follows.
Sodium hydride, 60% dispersion in mineral oil (CAS-RN: 7646-69-7)(429 mg, 10.7mmol, 1.3 eq) was suspended in 20 mL THF at 0C and the reactants tert-butyl(35,4R)-3-fluoro-4-hydroxypiperidine- 1 -carboxylate (CAS-RN: 955028-88-3) (1900 mg, 8.7 mmol. 1.05 eq), which was synthesized according to Shaw et al. (JOC, 2013, 78, 8892-97.) dissolved in 10 mL THF and 2-chloro-5-nitropyridine (CASRN: 4548-45-2) (1308 mg, 8.3 mmol, 1 eq) dissolved in 10 mL THF were added. Thereaction mixture was allowed to warm up to room temperature, and then it was cooled down to 0C again for about 10 minutes and stirred for 5 h at rt. All volatile components were removed in vacuo and the residue was partitioned between ethyl acetate and water. The combined organic phases were washed with brine and dryed by the use of a Whatman filter. The volatile components of the organic phasewere removed in vacuo. The final purification of this crude material was achieved via preparative MPLC (Biotage Isolera; 100 g KP cartridge: n-hexane/ethyl acetate:1:9 – 2:8) to give 2.4 g (85% yield of theory) of the title compound.1H-NMR (400 MHz, DMSO-d6): oe [ppm] = 1.20 – 1.31 (m, 1 H), 1.40 (5, 9 H), 1.70 -1.96 (m, 2 H), 2.78 – 3.28 (m, 2 H), 3.83 – 4.03 (m, 1 H), 4.15 (5 br, 1 H), 5.31 -5.53 (m, 1 H), 7.08 (d, 1 H), 8.49 (dd, 1 H), 9.06 (d, 1 H)., 1174020-40-6
The synthetic route of 1174020-40-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113920; (2015); A1;,
Piperidine – Wikipedia
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