Sodium Azide → (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine

Participants

Reaction Conditions

Reaction Steps

(3R,4R)-1-Benzyloxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpyrrolidine (125 mg) was dissolved in N,N-dimethylformamide (3 mL) and sodium azide (50.0 mg) was added. The mixture was stirred at 100° C. for 1 hour and was then concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (5 mL) and the solution was washed with water (2×1 mL), followed by drying over anhydrous sodium sulfate and concentration under reduced pressure. The resulting residue was purified on a silica gel column (eluant=ethyl acetate) to give 91.0 mg of (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine as a milky white syrup-like product. The compound was identical to the compound obtained by Process (A).

Provenance & Evidence