Methyl iodide → tert-Butyl Hexahydro-4-methyl-3-oxo-1H-1,4-diazepine-1-carboxylate

HRID 2211834

Reaction equation

HRID 2211834 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:10][CH2:9][CH2:8][CH2:7][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]1.I[CH3:19]>CN(C=O)C.[Cl-].[NH4+]>[CH3:19][N:10]1[CH2:9][CH2:8][CH2:7][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5][C:4]1=[O:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21962087tert-Butyl 3-oxo-1,4-diazepane-1-carboxylate

Product 1

HCID 21962086tert-Butyl Hexahydro-4-methyl-3-oxo-1H-1,4-diazepine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Sodium hydride (103 mg) was added to a stirred solution of tert-butyl hexahydro-3-oxo-1H-1,4-diazepine-1-carboxylate in DMF (5 mL) at 0° C. After 1 h, iodomethane (0.15 mL) was added, and the resultant mixture was stirred at 0° C., then room temperature overnight. It was diluted with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was separated, washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, and concentrated to give the product, which was used without further purification.

Workup

  1. customroom temperature overnight
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed sequentially with saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give the product, which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-b325bacc98db4c4fa7d085a593171d7f
Source dataset
uspto-grants-2006_09
Patent number
US07101871B2

Linked notes

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