Methanol → HCID 69428532, compound

Participants

Reaction Steps

A solution of 0.91 g (4.08 mmol) triethyl phosphonoacetate in 10 ml THF was first treated with 0.18 g (4.08 mmol) 55% NaH and after cooling (−78° C.) with 1.2 g (3.4 mmol) (2S,4R)-2-formyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester. The reaction was warmed up to room temperature and stirred over night. The solution was cooled (0° C.) and treated with 1 ml MeOH followed by 10 ml saturated aqueous Na/K-tartrate and after 10 min with aqueous 10% NaHCO3 solution. The aqueous phase was filtered, extracted (EtOAc 2×) and the organic phase was dried (Na2SO4), evaporated and purified on silica gel column (Hexane/EtOAc 9:1 to 7:3) to give 0.57 g (40%) of (2S,4R)-2-(2-ethoxycarbonyl-vinyl)-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, MS: 422 (MH+).

Provenance & Evidence