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

Temperature

60 °C

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).

1. temperatureWhile the mixture was cooled on an ice bath
2. washwas washed with a saturated aqueous solution of sodium chloride (2×50 mL)
3. dry with materialby drying over anhydrous sodium sulfate and concentration
4. customThe resulting residue was purified on silica gel column (eluant=ethyl acetate:hexane=2:1)

ORD record

ord-0fcefc1b56864573978d597b868bc2f8

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153851B2