Water → (R)-tert-Butyl(1-methyl-2-oxopiperidin-3-yl)carbamate

HRID 446943Notes

Reaction equation

HRID 446943 reaction equation
[O:1]=[C:2]1[C@H:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Na+].I[CH3:19].O>CN(C)C=O>[CH3:19][N:3]1[CH2:4][CH2:5][CH2:6][C@@H:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[C:2]1=[O:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 45092193(R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate

Product 1

HCID 67388684(R)-tert-Butyl(1-methyl-2-oxopiperidin-3-yl)carbamateYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-tert-butyl 2-oxopiperidin-3-ylcarbamate (642 mg, 3.00 mmol) in N,N-dimethylformamide (3 mL) at room temperature was added sodium hydride (132 mg, 3.3 mmol). The reaction mixture stirred for 30 min, then iodomethane (206 μL, 3.3 mmol) was added and stirring was continued for 1 h. The reaction mixture was poured into water (50 mL) and extracted with EtOAc (100 mL), using a continuous extractor apparatus overnight. The organic extract was evaporated to dryness under vacuum and the crude residue was purified by SiO2 chromatography (23 g, CH2Cl2/MeOH/NH4OH, 100:0:0 to 94:5.7:0.3) to give 310 mg (45%) of (R)-tert-butyl 1-methyl-2-oxopiperidin-3-ylcarbamate as a colorless viscous oil.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. extractionextracted with EtOAc (100 mL)
  4. customa continuous extractor apparatus overnight
  5. extractionThe organic extract
  6. customwas evaporated to dryness under vacuum
  7. customthe crude residue was purified by SiO2 chromatography (23 g, CH2Cl2/MeOH/NH4OH, 100:0:0 to 94:5.7:0.3)

Sources & evidence

ORD record
ord-2c0ca4a7406948369a3cb1b46451d050
Source dataset
uspto-grants-2013_07
Patent number
US08481541B2

Reaction notes

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