Benzyl Bromide → (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid

Participants

Reaction Steps

A solution of 138 mg (0.4 mmol) (2S,4R)-1-Methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-2-carboxylic acid in 8 ml THF was treated at −78° C. with 0.83 ml (1.24 mmol, 1.5 M THF solution) of LDA. After 30 min 0.17 ml (1.4 mmol) benzylbromide were added and warmed up to RT over night. The reaction was poured into aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous 10% NaCl solution and dried over Na2SO4 to give 242 mg (quantitativ) crude (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid.

Provenance & Evidence