P. Kotian, Tsu-Hsing Lin, Y. El-Kattan
Feb 17, 2005
Citations
0
Influential Citations
26
Citations
Journal
Organic Process Research & Development
Abstract
(3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol (1), which is a useful intermediate for the synthesis of various bioactive molecules, has been synthesized in 51% overall yield by 1,3-dipolar cycloaddition reaction from the dipolarophile, (E)-3-benzyloxypropenoyl-(2‘S)-bornane-10,2-sultam (5), and the achiral ylide precursor, N-(benzyl)-N-(methoxymethyl)-N-(trimethylsilylmethyl)amine (6), without using chromatography and the subsequent reduction with LAH and catalytic hydrogenation. The diastereomers 7 and 8 were separated by crystallization, and efficient procedures were developed for the subsequent reactions to afford 1.