Carbon tetrabromide → (3R,4S)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine

Participants

Reaction Conditions

Reaction Steps

(3R,4S)-[1-Benzyloxycarbonyl-4-hydroxypyrrolidin-3-yl]methanol (2.33 g), sodium azide (1.81 g), triphenylphosphine (2.67 g), and N,N-dimethylformamide (46 mL) were mixed with one another. While this mixture was cooled on an ice bath, a dichloromethane solution (10 mL) of carbon tetrabromide (3.38 g) was added dropwise. The reaction mixture was stirred for 13 hours at room temperature and additional 3 hours at 60° C., followed by addition of methanol (3 mL) and concentration under reduced pressure. The resulting residue was dissolved in ethyl acetate (200 mL) and was washed with a saturated aqueous solution of sodium chloride (2×50 mL), followed by drying over anhydrous sodium sulfate and concentration under reduce pressure. The resulting residue was purified on a silica gel column (eluant=ethyl acetate:hexane=2:1) to give 2.18 g of (3R,4S)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine as a milky white syrup-like product.

Provenance & Evidence