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

Process B: (3R,4R)-3-Azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine (1.79 g) was dissolved in toluene (56 mL). While this solution was chilled in an ice water bath, 1,8-diazabicyclo[5.4.0]undec-7-ene (2.03 mL) was added, followed by dropwise addition of perfluoro-1-octanesulfonyl fluoride (2.80 mL) and stirring for 1 hour. The insoluble material in the reaction mixture was filtered and washed with toluene. The filtrate and the washings were combined and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=2:1) to give (3R,4S)-3-azidomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine as a pale brown syrup (1.58 g). This compound was identical to the compound obtained by Process A.

1. temperatureWhile this solution was chilled in an ice water bath
2. filtrationThe insoluble material in the reaction mixture was filtered
3. washwashed with toluene
4. concentrationconcentrated under reduced pressure
5. customThe resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=2:1)

ORD record

ord-bbdbe1862a494bc6b57e56c225f51c22

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514451B2