Sodium hydride → 1414837-14-1
Reaction equation
[C:1]1([C@@H:7]2[CH2:11][NH:10][CH2:9][C@H:8]2[NH:12]C(=O)[O-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].FC(F)(F)S(O[CH2:24][C:25]([F:28])([F:27])[F:26])(=O)=O>CN(C=O)C>[C:1]1([C@@H:7]2[CH2:11][N:10]([CH2:24][C:25]([F:28])([F:27])[F:26])[CH2:9][C@H:8]2[NH2:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Racemic tert-butyl (3R,4S) and (3S,4R)-4-phenylpyrrolidin-3-ylcarbamate (260 mg, 0.991 mmol) was taken up in DMF (5 ml) and cooled to 0° C. NaH (59.5 mg, 1.487 mmol) was added slowly. The reaction was allowed to stir for 10 minutes at 0° C. before adding 2,2,2-trifluoroethyl trifluoromethanesulfonate (345 mg, 1.487 mmol). The reaction continued to stir at 0° C. for 1 hour and was then allowed to reach room temperature and continue stirring for 16 hours. LC/MS in showed full conversion to desired product. Saturated NH4Cl was added slowly. EtOAc and water were added. Our products were extracted into EtOAc (3×). The combined organic layers were then washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by MPLC SNAP 25 g 0-25% EtOAc/hexanes gave racemic tert-butyl (3R,4S) and (3S,4R)-4-phenyl-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl)carbamate (258 mg, 0.749 mmol, 76% yield). MS ESI calc'd. For C17H24F3N2O2 [M+1]+ 345, found 345.
Workup
- stirringto stir at 0° C. for 1 hour
- customto reach room temperature
- stirringcontinue stirring for 16 hours
Sources & evidence
- ORD record
- ord-6e13a3d7ca514c7b9ae16aef4043a85a
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023865B2
Reaction notes
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