Perfluorooctanesulfonyl fluoride → (3S,4S)-1-benzyloxycarbonyl-3-bromomethyl-4-fluoropyrrolidine

Temperature

2 °C

Process B: (3S,4R)-1-Benzyloxycarbonyl-3-bromomethyl-4-hydroxypyrrolidine (492 mg) was dissolved in toluene (1 mL). To this solution, 1,8-diazabicyclo[5.4.0]undec-7-ene (0.35 mL) was added and perfluoro-1-octanesulfonylfluoride (0.42 mL) was subsequently added dropwise while the mixture was chilled in an ice water bath. The reaction mixture was stirred at 2° C. for 30 min and then at room temperature for 5 hours. Subsequently, the mixture was poured on a silica gel pad and was eluted with ethyl acetate (80 mL). The eluate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=2:1) to give (3S,4S)-1-benzyloxycarbonyl-3-bromomethyl-4-fluoropyrrolidine as a milky white syrup (421 mg).

1. temperaturewas chilled in an ice water bath
2. waitat room temperature for 5 hours
3. additionSubsequently, the mixture was poured on a silica gel pad
4. washwas eluted with ethyl acetate (80 mL)
5. concentrationThe eluate was concentrated under reduced pressure
6. customthe resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=2:1)

ORD record

ord-d9709360187746f1875ba57cc83e3e78

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514451B2