US 7,514,573 B2
Processes for the manufacture of chiral and racemic forms of 3-aminotetrahydrofurans, their salts and derivatives
Muhammed Majeed, Piscataway, N.J. (US); Kalyanam Nagabhushanam, Piscataway, N.J. (US); Sivaprskash Kurumanghat Balakrishnan, Bangalre (India); Savita Ganjihal, Bangalore (India); Rajendran Ramanujam, Bangalore (India); Rattan Sood, Bangalre (India); and Subbalakshmi Prakash, Piscataway, N.J. (US)
Assigned to Sami Labs Ltd, Bangalore (India)
Filed on Apr. 11, 2007, as Appl. No. 11/733,772.
Prior Publication US 2008/0255377 A1, Oct. 16, 2008
Int. Cl. C07D 307/22 (2006.01)
U.S. Cl. 549—480 8 Claims
 
1. A process for the manufacture of 3-(S)-aminotetrahydrofuran comprising the steps of
a) reduction of a compound with structure I to a compound with structure II with the aid of a hydride reducing agent;

OG Complex Work Unit Drawing
wherein R1 is selected from the group consisting of C1-C6 straight chain and branched alkyls and —CH2-Aryl; R2 is selected from a group consisting of C1-C6 straight chain and branched alkyls, —CH2-Aryl, phenyl and substituted phenyl;
b) cyclizing the compound with structure II with the aid of sulfonic acids to structure III;
c) hydrolyzing the compound using a base with structure III to 3-(S)-aminotetrahydrofuran; and
d) recovering 3-(S)-aminotetrahydrofuran as its hydrochloride or p-toluenesulfonate salt or as base itself.