Methyl 3-(4,4-difluorocyclohexyl)-4-nitrobutanoate → 4-(4,4-Difluorocyclohexyl)pyrrolidin-2-one
Reaction equation
[F:1][C:2]1([F:18])[CH2:7][CH2:6][CH:5]([CH:8]([CH2:14][N+:15]([O-])=O)[CH2:9][C:10](OC)=[O:11])[CH2:4][CH2:3]1>CO.[Ni]>[F:1][C:2]1([F:18])[CH2:7][CH2:6][CH:5]([CH:8]2[CH2:14][NH:15][C:10](=[O:11])[CH2:9]2)[CH2:4][CH2:3]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
Methyl 3-(4,4-difluorocyclohexyl)-4-nitrobutanoate a1-20 (1.390 g, 5.24 mmol, 1 eq) is dissolved in methanol (35 ml) and Raney Nickel (50% in water, 200 mg, 1.7 mmol, 0.3 eq) is rinsed 3 times with methanol and added to the solution. The mixture is heated overnight at 50° C. under a H2 atmosphere (20 bars). The mixture is then filtered and the filtrate is evaporated under reduced pressure to afford 4-(4,4-difluorocyclohexyl)pyrrolidin-2-one a1-26.
Workup
- additionadded to the solution
- filtrationThe mixture is then filtered
- customthe filtrate is evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-dfc06911d2ab4d1ead1b1b303bb5d109
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067930B2
Reaction notes
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