3-(4-(4-(Benzyloxy)phenyl)-3,3-difluoropiperidin-1-yl)-1-(3-fluoro-4-methylbenzyl)pyrrolidin-2-one → 3-(3,3-Difluoro-4-(4-hydroxyphenyl)piperidin-1-yl)-1-(3-fluoro-4-methylbenzyl)pyrrolidin-2-one
Reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][N:18]([CH:21]3[CH2:25][CH2:24][N:23]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([F:34])[CH:28]=4)[C:22]3=[O:35])[CH2:17][C:16]2([F:37])[F:36])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[F:37][C:16]1([F:36])[CH:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[CH2:20][CH2:19][N:18]([CH:21]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([F:34])[CH:28]=3)[C:22]2=[O:35])[CH2:17]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 3-(4-(4-(benzyloxy)phenyl)-3,3-difluoropiperidin-1-yl)-1-(3-fluoro-4-methylbenzyl)pyrrolidin-2-one (0.45 g, 0.89 mmol, mixture of diastereomers from step D) in MeOH (8 mL) at rt was added 0.56 g of 10% Pd/C and the reaction mixture was stirred at rt under a hydrogen atmosphere overnight. The catalyst was removed by filtration through Celite and the solvent was removed in vacuo. The residue was subjected to HPLC purification (method E) to yield 200 mg of 3-(3,3-difluoro-4-(4-hydroxyphenyl)piperidin-1-yl)-1-(3-fluoro-4-methylbenzyl)pyrrolidin-2-one as a mixture of four diastereoisomers.
Workup
- customThe catalyst was removed by filtration through Celite
- customthe solvent was removed in vacuo
- customThe residue was subjected to HPLC purification (method E)
Sources & evidence
- ORD record
- ord-af0384023d834cfcaf58c4bfab269d32
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221796B2
Reaction notes
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