Phenylacetylene → HCID 70001567, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7.69 ml (70 mmol) phenylacetylen in 140 ml THF was treated at −25° C. with 43.8 ml (70 mol) n-butyllithium (1.6 M in hexane). The reaction was warmed up to −10° C. for 1 h. A solution of 7.46 g (14 mmol) (2S,4R)-2-(Methoxy-methyl-carbamoyl)-4-tritylsulfanyi-pyrrolidine-1-carboxylic acid butyl ester in 110 ml THF was then added. After 20 min the reaction was neutralized with 190 ml of an aqueous 10% KHSO4 solution. The mixture was extracted with aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous saturated 10% NaCl, dried over Na2SO4, evaporated and purified by flash-chromatography on silicagel (Hexane/EtOAc 9:1) to give 6.54 g (81%) of (2S,4R)-2-(3-Phenyl-propynoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid butyl ester, MS: 574 (MH+).

Provenance & Evidence