HCID 10199020, compound → methyl (1S,3R,4S)-3-{[(tert-butoxy)carbonyl]amino}-4-hydroxycyclopentane-1-carboxylate

Participants

Reaction Steps

Palladium-on-carbon (1 g, 10 wt %) was added under nitrogen to a solution of (3S,4R)-4-tert-butoxycarbonylamino-3-hydroxycyclopent-1-enecarboxylic acid methyl ester (70 g, 0.29 mol) in methanol (300 ml). The reaction mixture was transferred to a bomb, and, after purging with nitrogen and then hydrogen, a hydrogen pressure of 2 bar was applied and the reaction stirred for 14 h (periodically, additional hydrogen was added to the reaction, to reestablish and initial reaction pressure). The pressure was released and the bomb purged with nitrogen. The reaction mixture was cautiously filtered through Celite® and then concentrated to give the title compound as a syrup of 90% d.e. in quantitative yield.

Provenance & Evidence