Methyl chloroformate → Methyl 4-oxopiperidine-1-carboxylate
Reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:17]([O:19][CH3:20])=[O:18]>O>[O:9]=[C:6]1[CH2:7][CH2:8][N:3]([C:17]([O:19][CH3:20])=[O:18])[CH2:4][CH2:5]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-piperidone monohydrate hydrochloride (3.07 g, 20.0 mmol) in water (12 mL) cooled to 0° C. was added a cooled solution (also at 0° C.) of potassium carbonate (6.97 g, 50.4 mmol) in water (40 mL). Methyl chloroformate (2.80 g, 29.6 mmol) was added, and the mixture was allowed to stir for 2 h, still at 0° C. Then, the mixture was extracted with dichloromethane (3×40 mL), and the extract was dried over MgSO4, and concentrated. The obtained residue was chromatographed (silica gel, dichloromethane to 95:5 dichloromethane/methanol) to give the title compound (2.96 g, 94%) as a viscous clear liquid:
Workup
- extractionThen, the mixture was extracted with dichloromethane (3×40 mL)
- dry with materialthe extract was dried over MgSO4
- concentrationconcentrated
- customThe obtained residue was chromatographed (silica gel, dichloromethane to 95:5 dichloromethane/methanol)
Sources & evidence
- ORD record
- ord-61f6008b93fe4ad98b2c34c12bfb7ce5
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691828B2
Reaction notes
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