(2S)-2-[(1R,2S)-2-benzyloxycarbonyl-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester → (2S)-2-[(R,2S)-2-carboxy-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

A mixture of (2S)-2-[(1R,2S)-2-benzyloxycarbonyl-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (4.4 g, 11.2 mmol) and Pd(OH)2 on carbon(ca.20 wt %, 2.0 g) in EtOH (50 mL) was stirred at room temperature under H2 atmosphere. After being stirred at room temperature for 14 hr, the mixture was filtrated through a pad of celite and washed with MeOH. The filtrate and washings were combined and concentrated in vacuo to give a crude gum, which was purified by flush column chromatography (hexane:AcOEt=1:1) to give (2S)-2-[(R,2S)-2-carboxy-1-methylsulfanyl-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a gum (3.39 g, 98%).

Provenance & Evidence