Patent ID: 8445700

Claim:
A process for the preparation of optically active N-benzyl-3-hydroxypyrrolidine from (−)-vasicine comprising the steps: (a) reacting (−)-vasicine of formula 3 (b) with a reducing agent in an organic or aqueous medium at a temperature ranging between 0° C. to 40° C. for a period ranging between 10 min to 1 hr to obtain aniline derivative of formula 4, (c) diazotisation of the aniline derivative of formula 4 and deamination of diazonium intermediate to obtain (S)-(−)-N-benzyl-3-hydroxypyrrolidine of formula 1, (d) reacting (S)-(−)-N-benzyl-3-hydroxypyrrolidine of formula 1 with a reagent system selected from a group comprising triphenyl phoshine, diethyl azodicarboxylate (DEAD), and diisopropyl azodicarboxylate (DIAD), at a temperature ranging between 0° C. to 25° C. for period ranging between 1 hr to 16 hr followed by addition of an acid selected from a group of an organic acid consisting of formic acid, acetic acid, and propionic acid and adjusting the pH in the range of 8-9 by addition of ammonia to obtain the intermediate compound of formula 5, wherein R is selected from the group consisting of HCO, CH 3 CO, CH 3 CH 2 CO, and CH 3 CH 2 CH 2 CO; and (e) hydrolyzing the intermediate compound of formula 5 by reacting with a base at a temperature ranging between 0° C. to 25° C. for a period ranging between 1 hr to 3 hr to obtain the (R)-(+)-N-benzyl-3-hydroxypyrrolidine of formula 2 selected from a group consisting of lithium hydroxide, sodium hydroxide, and potassium hydroxide