Ethyl 4-piperidinecarboxylate → HCID 118020688, compound
Reaction equation
CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[NH:20]1[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]1.Br[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH:39]([F:41])[F:40])=[CH:34][CH:33]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[F:40][CH:39]([F:41])[O:38][C:35]1[CH:36]=[CH:37][C:32]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]2)=[CH:33][CH:34]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
Sodium tert-butoxide (2.29 g, 23.8 mmol), palladium(II) acetate (428 mg, 1.91 mmol), and tri-tert-butylphosphine (370 μL, 1.52 mmol) were added to a solution of ethyl piperidine-4-carboxylate (3.52 mL, 22.9 mmol) and 1-bromo-4-(difluoromethoxy)benzene (4.25 g, 19.1 mmol) in toluene (122 mL), and the mixture was stirred at 80° C. for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-90/10] to obtain the title compound (3.17 g, yield: 56%).
Workup
- extractionfollowed by extraction with ethyl acetate
- washThe obtained organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-90/10]
Sources & evidence
- ORD record
- ord-5a1039c3ce624d1d81ed159847190878
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150575B2
Reaction notes
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