HCID 15537958, compound → HCID 54038063, compound

Participants

Reaction Steps

A mixture of (2S,4R)-4-t-butyldimethylsilyloxy-2-hydroxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (10.0 g), methanol (100 ml) and 10% palladium on carbon (1.0 g), was stirred in a nitrogen stream at ambient temperature for 3 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give (2S,4R)-4-t-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine. To a solution of the compound obtained above in tetrahydrofuran (100 ml) was added di-t-butyl dicarbonate (5.60 g) and the mixture was refluxed for 30 minutes. The reaction mixture was concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (160 g) and eluted with chloroform to give (2S,4R)-1-t-butoxycarbonyl-4-t- butyldimethylsilyloxy-2-hydroxymethylpyrrolidine (7.97 g).

Provenance & Evidence