Benzyl chloroformate → 1-Boc-4-Cbz-amino-piperidine
Reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:28]([O:27][C:25]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1Participants
6
Procedure
tert-Butyl 4-aminopiperidine-1-carboxylate (10 g, 49.9 mmol), N,N-diisopropylethylamine (26 ml, 149 mmol), benzyl chloroformate (8.5 ml, 59.5 mmol) and dichloromethane (dehydrated) (300 ml) were mixed under ice-cooling. The resulting mixture was stirred at room temperature for one hour. An aqueous saturated sodium bicarbonate solution was added to the reaction mixture, which was extracted with dichloromethane three times. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (silica gel, elution solvent: ethyl acetate/heptane) to give the title compound (13.1 g, yield 78.5%).
Workup
- temperaturecooling
- extractionwas extracted with dichloromethane three times
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off
- customThe residue was purified by silica gel column chromatography (silica gel, elution solvent: ethyl acetate/heptane)
Sources & evidence
- ORD record
- ord-a7fae4ba6124453ca28d8f79c52ffbc0
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476301B2
Reaction notes
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