Water → HCID 57516591, compound

HRID 1620751Notes

Reaction equation

HRID 1620751 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][CH2:11][NH:10][C:9]1=[O:14])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:19].O>CN(C=O)C>[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH3:19])[C:9]1=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21260262tert-Butyl (2-oxopiperidin-3-yl)carbamate

Product 1

HCID 57516591HCID 57516591, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl(2-oxopiperidin-3-yl)carbamate (1714 mg) in DMF (20 mL) was added 60% sodium hydride (480 mg, containing mineral oil) under ice-cooling. The reaction mixture was stirred at room temperature for 30 min, and iodomethane (1703 mg) was added. The reaction mixture was stirred at room temperature overnight, water was added, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (530 mg).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-73b566ad2f4743628e9a895727fa18cb
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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