Hydrochloric Acid → HCID 67705486, compound

Participants

Reaction Steps

To a solution of (2S,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-[(Z)-2-(pyridin-3-yl)vinyl]-pyrrolidine (4.70 g) in methanol (50 ml) was added conc. hydrochloric acid (2.68 ml) at ambient temperature with stirring and the mixture was allowed to stand at the same temperature for 3 hours. To the reaction mixture was added 28% sodium methoxide-methanol solution (6.20 ml) under ice-cooling with stirring and the resulting insoluble material was filtered off. The filtrate was evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (150 g) eluting with a mixture of chloroform and methanol (9:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-1-benzyloxycarbonyl-4-hydroxy-2-[(Z)-2-(pyridin-3-yl)vinyl]-pyrrolidine (5.20 g).

Provenance & Evidence