Perfluorooctanesulfonyl fluoride → HCID 66704853, compound
Reaction equation
[Br:1][CH2:2][C@@H:3]1[C@@H:7](O)[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.N12CCCN=C1CCCCC2.[F:27]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F>C1(C)C=CC=CC=1>[Br:1][CH2:2][C@@H:3]1[C@H:7]([F:27])[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2 °C
Procedure
Process B: (3S,4R)-3-Bromomethyl-1-tert-butoxycarbonyl-4-hydroxypyrrolidine (561 mg) was dissolved in toluene (20 mL). To this solution, 1,8-diazabicyclo[5.4.0]undec-7-ene (0.50 mL) was added and perfluoro-1-octanesulfonylfluoride (0.93 mL) was then added dropwise while the mixture was chilled in an ice water bath. After stirred at 2° C. for 1 hour, the reaction mixture was poured on a silica gel pad and was eluted with ethyl acetate (100 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)-3-bromomethyl-1-tert-butoxycarbonyl-4-fluoropyrrolidine as a yellow oil (447 mg).
Workup
- temperaturewas chilled in an ice water bath
- additionthe reaction mixture was poured on a silica gel pad
- washwas eluted with ethyl acetate (100 mL)
- concentrationThe eluate was concentrated under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-0d6dc8abee5a46a9bc98d451e9ec3184
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514451B2
Reaction notes
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