Triethylamine → (2S,4S)-1-[2-(benzenesulfonyloxy)acetyl]-4-fluoropyrrolidine-2-carbonitrile
Reaction equation
[C:1]1([S:7]([O:10][CH2:11][C:12]([N:14]2[CH2:18][C@@H:17]([F:19])[CH2:16][C@H:15]2[C:20]([NH2:22])=O)=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(#N)C>[C:1]1([S:7]([O:10][CH2:11][C:12]([N:14]2[CH2:18][C@@H:17]([F:19])[CH2:16][C@H:15]2[C:20]#[N:22])=[O:13])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
(2S,4S)-1-[2-(benzenesulfonyloxy)acetyl]-4-fluoropyrrolid ine-2-carboxamide (516 mg) was dissolved in acetonitrile (10 mL) and triethylamine (0.52 mL) was added to the solution. While this mixture was cooled in an ice bath, trifluoroacetic anhydride (0.27 mL) was added dropwise and the mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was concentrated under reduced pressure. Water (5 mL) was added to the residue and the resulting crystal was collected by filtration. The filtered solid was washed with water and was dried under reduced pressure to give (2S,4S)-1-[2-(benzenesulfonyloxy)acetyl]-4-fluoropyrrolidine-2-carbonitrile as a white crystal (339 mg, 70% yield).
Workup
- temperatureWhile this mixture was cooled in an ice bath
- concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
- additionWater (5 mL) was added to the residue
- filtrationthe resulting crystal was collected by filtration
- washThe filtered solid was washed with water
- customwas dried under reduced pressure
Sources & evidence
- ORD record
- ord-8bc11f62e3ff4b8185be0d09735e96c1
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915427B2
Reaction notes
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