HCID 54440118, compound → HCID 54188385, compound

Participants

Reaction Steps

A solution of (2S,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-(carbamoylmethyloxymethyl)pyrrolidine (0.60 g) in a mixture of trifluoroacetic acid (3 ml) and anisole (0.6 ml) was stirred at ambient temperature for 1 hour. The mixture was concentrated under reduced pressure to give (2S,4R)-2-(carbamoylmethyloxymethyl)-4hydroxypyrrolidine. To a solution of the compound obtained above in a mixture of water (20 ml) and tetrahydrofuran (20 ml) was dropwise added a solution of 4-nitrobenzyloxycarbonyl chloride (0.50 g) in tetrahydrofuran (5 ml) under icecooling with stirring, keeping the pH between 8.5-9.5 with 1N aqueous sodium hydroxide. The mixture was stirred at the same condition for 1 hour and extracted with ethyl acetate (50 ml). The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (20 g) and eluted with a mixture of methanol and chloroform (1:99 and then 2:98 V/V) to give (2S,4R)-2-(carbamoylmethyloxymethyl)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.32 g).

Provenance & Evidence