Methylamine → Tert-butyl 4-(methylcarbamoyl)piperidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](O)=[O:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[CH2:18][N:19](CC)CC.C(OC(Cl)=O)C(C)C.CN>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](=[O:13])[NH:19][CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 1-t-butoxycarbonyl-iso-nipecotic acid (10 g) and Et3N (5.92 mL) in THF (32 mL) was added drop-wise iso-butylchloroformate (5.66 mL) at 0° C. The resulting mixture was stirred at 0° C. for 30 min before diluted with THF (120 mL) and added 2M methylamine (80 mL). The reaction mixture was stirred overnight at room temperature. Excess THF was removed under vacuum. The residue was taken into H2O and extracted into EtOAc. The organic extracts were washed with 1N NaOH, followed by brine. After dried over Na2SO4, it was concentrated to give the crude product.
Workup
- stirringThe reaction mixture was stirred overnight at room temperature
- customExcess THF was removed under vacuum
- extractionextracted into EtOAc
- washThe organic extracts were washed with 1N NaOH
- dry with materialAfter dried over Na2SO4, it
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-d7a4632288464b91933d6703961f99f6
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410119B2
Reaction notes
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