Journal of Organic & Inorganic Chemistry

Novel asymmetric synthesis of (S)-Ketamine anesthetic drug using the chiral tert-butanesulfinamide

6^th Edition of International Conference and Exhibition on Organic Chemistry
August 16-17, 2018 Dublin, Ireland

Abdollah Javidan

University of Eyvanekey, Iran

Posters & Accepted Abstracts: J Org Inorg Chem

DOI: 10.21767/2472-1123-C4-012

Abstract

2-(2-chlorophenyl)-2-(methylamino)-cyclohexanone (Ketamine), has been widely used as an anesthetic and analgesic drug. In this research work, at first the 2- (N-piperidino methyl)-1- phenyl cyclohexyl amine stating material (1), was prepared from cyclohexanone piperidine by Mannich reaction. Then, the sulfinylimin (2) was synthesized by condensation of tert-butanesulfinamide (tBS) with aminoketone (1) in presence of Ti(OEt)4 in 85% yield. The new chiral center was induced in (2) using Grignard reagent as nucleophile at -78°C and 75% yield. after multi step reaction including methylation of (3) and Hoffman elimination of (4) and deprotection of (5), finally, the (S)- ketamine was synthesized under ozonolize reaction of alken (6) in good yield and enantioselectivity (95% yield and %85 ee).

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