Ammonium formate → HCID 905991, compound
Reaction equation
C([N:8]1[CH2:13][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>O.CO.[Pd]>[C:14]1([C@H:12]2[C@@H:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:10][CH2:9][NH:8][CH2:13]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of 9.98 g of ethyl 1-benzyl-5-phenyl-1,2,3,6-tetrahydropyridine-4-carboxylate, 10.31 g of ammonium formate, and 90 mL of methanol was added 1.49 g of 10% palladium/carbon while suspending it in 10 mL of water and 10 mL of methanol. The reaction mixture was vigorously stirred at 60° C. for 2 hours. After cooling to room temperature, the insolubles were filtered on a celite layer, and the filtrate was concentrated under reduced pressure. To the obtained residue was added chloroform, followed by washing with saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and dried to obtain 7.09 g of a pale yellow oily substance of ethyl rel-(3R,4S)-3-phenylpiperidine-4-carboxylate as a crude product. ESI+: 234
Workup
- temperatureAfter cooling to room temperature
- filtrationthe insolubles were filtered on a celite layer
- concentrationthe filtrate was concentrated under reduced pressure
- additionTo the obtained residue was added chloroform
- washby washing with saturated aqueous sodium bicarbonate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationAfter filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customdried
Sources & evidence
- ORD record
- ord-292c5df2faeb49ac9fdc89cdcbe71936
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153658B2
Reaction notes
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