Trityl chloride → HCID 11123509, compound

Participants

Reaction Steps

To a solution of (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-(cyanomethyl) pyrrolidine (8.20 g) in tetrahydrofuran (40 ml) and methanol (40 ml) was added a 28% sodium methoxide in methanol solution (6.03 ml) at ice-cooling. After stirring at ice-cooling for 30 minutes, chlorotriphenylmethane (8.31 g) was added to the cold solution. After stirring at the same temperature for 2 hours, the solution was poured into a mixture of ethyl acetate and water. The separated organic layer was washed with aqueous sodium chloride solution twice, dried over magnesium sulfate and evaporated. The residue was subjected to a column chromatography on silica gel (eluent; n-hexane:ethyl acetate=5:1) to give (2R,4S)-1-allyloxycarbonyl-2-cyanomethyl-4-(triphenylmethylthio)pyrrolidine (11.7 g).

Provenance & Evidence