Reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1>O1CCCC1CO.[OH-].[Pd+2].[OH-]>[NH3:8].[F:32][C:29]([F:30])([F:31])[C:26]1[CH:25]=[CH:24][C:23]([C:18]2[C:17]([C:15]([NH:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:16])=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:28][CH:27]=1Participants
5
Reactant 1
Product 2
Reagents, catalysts & solvents 2
Procedure
To a solution of the 1-benzyl-4-(4′-trifluoromethylbiphenyl-2-carbonylamino)piperidine (1.47 g) obtained in Example 8a) in tetrahydrofuran-methanol (1:1; 50 mL) was added palladium hydroxide (300 mg) in a stream of argon under ice-cooling. The mixture was stirred for one day at normal pressure under hydrogen atmosphere, and further stirred for one day at normal pressure under hydrogen atmosphere after further addition of palladium hydroxide (300 mg). The reaction mixture was filtered through a Celite pad and washed with methanol. The filtrate and the washings were combined, concentrated in vacuo and purified by column chromatography on silica gel with chloroform:methanol:aqueous ammonia=100:10:1 to give the title compound (1.03 g).
Workup
- temperaturecooling
- stirringfurther stirred for one day at normal pressure under hydrogen atmosphere
- filtrationThe reaction mixture was filtered through a Celite pad
- washwashed with methanol
- concentrationconcentrated in vacuo
- custompurified by column chromatography on silica gel with chloroform
Sources & evidence
- ORD record
- ord-acf22412513b4430899df264ef800621
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538140B2
Linked notes
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