Tert-butyl 3-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate → tert-Butyl 3-acetylpiperidine-1-carboxylate

HRID 1465709Notes

Reaction equation

CON(C)[C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5].[CH3:20][Mg]Br>C1COCC1>[C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:7]1)(=[O:5])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

Tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (8.17 g, 30 mmol) was dissolved in THF (100 mL) and cooled to 0° C., methylmagnesium bromide (3.0 M in Et2O, 11 mL, 33 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. After quench with saturated NH4Cl, the reaction mixture was extracted with EtOAc, dried and concentrated. The crude product was column purified with mixture of hexane and EtOAc to give tert-butyl 3-acetylpiperidine-1-carboxylate (4.8 g).

Workup

temperatureThe reaction mixture was warmed to room temperature
customAfter quench with saturated NH4Cl
extractionthe reaction mixture was extracted with EtOAc
customdried
concentrationconcentrated
custompurified with mixture of hexane and EtOAc

Sources & evidence

ORD record: ord-6c45a7c41d2a49748a83d3c5b41057ae
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999966B2

Reaction notes

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