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

Participants

Reaction Conditions

Reaction Steps

Process (B): (3R,4R)-[1-Benzyloxycarbonyl-4-hydroxypyrrolidin-3-yl]methanol (3.00 g), sodium azide (2.32 g), triphenylphosphine (3.43 g) and N,N-dimethylformamide (60 mL) were mixed with each other. While the mixture was cooled on an ice bath, a dichloromethane solution (14 mL) of carbon tetrabromide (4.34 g) was added dropwise. The reaction mixture was stirred for 25 hours at room temperature and additional 2 hours at 60° C., followed by addition of methanol (5 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 silica gel column (eluant=ethyl acetate:hexane=2:1) to give 2.94 g of (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine as a pale brown syrup-like product. This compound was identical to the compound obtained by Process (A).

Provenance & Evidence