Sodium Azide → (2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester

Participants

Reaction Conditions

Reaction Steps

A mixture of (2S,4S)-1-t-butoxycarbonyl-4-methylsulfonyloxy-2-methoxycarbonylpyrrolidine (27.7 g) and sodium azide (10.6 g) in dimethyl sulfoxide (350 ml) was stirred at 90° C. overnight and the solution was diluted with ethyl acetate (600 ml). The solution was washed successively with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to give (2S,4R)-4-azido-1-t-butoxycarbonyl-2-methoxycarbonylpyrrolidine (20.0 g) as a pale brown oil.

Provenance & Evidence