Process for preparing of stereoselective preparation of substituted piperidines

• Main Author: ROSEN TERRY J
• Format: Patent
• Language: English
• Published: 30.01.1997
• Edition: 6
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; APPARATUS THEREFOR; CHEMISTRY; GENERAL METHODS OF ORGANIC CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS

Prepn. of a (2S,3S)-3-(substd. amino)-2-substd.- piperidine of formula (I) from a (2S,3S)-3-amino-2-substd.-piperidine of formula (IV) comprises reaction with either: (a) a cpd. of formula R1COX, followed by treatment of the amide with a reducing agent; or (b) a cpd. of formula R1CHO in presence of a reducing agent; or (c) a cpd. of formula R1CH2X: R1 = aryl (indanyl, phenyl, or naphthyl), or heteroaryl (thienyl, furyl, pyridyl, or quinolyl), (all opt. substd. by Cl, F, Br, I, NO2, 1-10C alkyl (opt. substd. by 1-3F), 1-10C alkoxy (opt. substd. by 1-3F), 1-10C alkylthio, 1-10C alkysulphinyl, 1-10C alkylsulphonyl, phenyl, phenoxy, 1-10C alkylsulphonamido, 1-10C alkylsulphone 1-10C alkylamido, 1-10C alkylamino-di-1-10C alkyl (sic), CN, OH, 3-7C cyclalkyoxy, amino or 1-6C alkylamino (both opt. protected), HCONH, or 2-7C acylamido) or 3-7C cycloalkyl (opt. substd. by 1 or 2 of the above opt. substits.); R2 = thienyl, Ph2CH, naphthyl, or phenyl (opt. substd. with 1-3 of Cl, Br, F, I, 3-7C cycloalkoxy, 1-10C alkyl (opt. substd. by 1-3F) or 1-10C alkoxy (opt. substd. by 1-3F; and X = a leaving gp.