Benzyl chloroformate → 3-(Benzyloxycarbonylaminomethyl)-piperidine-1-carboxylic Acid Tert-butyl Ester
Reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>C1COCC1>[C:12]([O:11][C:9]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:4]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 3-(aminomethyl)-1-N-Boc-piperidine (1.64 g, 7.65 mmol) and TEA (1.6 mL, 11 mmol) in THF (5 mL) at 0° C., benzyl chloroformate (1.15 mL, 8.04 mmol) was added dropwise. The reaction was maintained at 0° C. for 1 h, then warmed to RT overnight. The solvent was evaporated in vacuo. The residue was taken up in a saturated solution of NH4Cl (aq) (15 mL) and extracted with EtOAc (10 mL). The organic layer was separated, dried over MgSO4, filtered and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica gel (1:4, EtOAc:hexane) to yield the title compound as a colorless oil. MS m/z: 349.3 (M+H). Calc'd. for C19H28N2O4-348.44.
Workup
- temperaturewarmed to RT overnight
- customThe solvent was evaporated in vacuo
- extractionextracted with EtOAc (10 mL)
- customThe organic layer was separated
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent was evaporated in vacuo
- customThe residue was purified by flash chromatography on silica gel (1:4, EtOAc:hexane)
Sources & evidence
- ORD record
- ord-0d151374df7540beb458ed41ccdfefa7
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196104B2
Reaction notes
Loading…