Phenethylamine → (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid benzyl-methyl-amide

Participants

Reaction Steps

A solution of 242 mg (0.4 mmol) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid in 4 ml THF was treated at 0° C. with 0.057 ml (0.44 mmol) N-benzylmethylamine, 92 mg (0.48 mmol) EDCI , 6.1 mg (0.04 mmol) HOBT and warmed up over night to RT. 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 after flash silicagel column (Hexane/EtOAc 4:1) 21 mg (10%) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carboxylic acid benzyl-methyl-amide, MS: 539 (MH+).

Provenance & Evidence