Methyl iodide → tert-butyl N-benzyloxy-N-methylcarbamate

HRID 976631

Reaction equation

HRID 976631 reaction equation
[H-].[Na+].C(ONC(=O)OC(C)(C)C)C1C=CC=CC=1.[C:19]([O:23][C:24](=[O:38])[N:25]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:26]C(C)C)([CH3:22])([CH3:21])[CH3:20].IC>CN(C)C=O>[CH2:31]([O:30][N:25]([CH3:26])[C:24](=[O:38])[O:23][C:19]([CH3:20])([CH3:21])[CH3:22])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 736159Tert-butyl N-(benzyloxy)carbamateHCID 19967428tert-butyl N-benzyloxy-N-(2-methylpropyl)carbamate

Product 1

HCID 14227181tert-butyl N-benzyloxy-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.48 g of 80% in mineral oil, 16 mmol) was added to a solution of tert-butyl N-benzyloxycarbamate (Compound 54 Part A, 3 g, 13 mmol) in N,N-dimethylformamide (25 mL). The reaction mixture was stirred for 20 minutes then iodomethane (1.1 mL, 18 mmol) was added dropwise with cooling in an ice bath. The resulting suspension was stirred at ambient temperature under a nitrogen atmosphere overnight. The reaction mixture was quenched with water (50 mL) then extracted with diethyl ether (150 mL). The organic layer was washed with water (5×50 mL), dried over magnesium sulfate then concentrated to provide 3.1 g of tert-butyl N-benzyloxy-N-methylcarbamate as a yellow oil.

Workup

  1. temperaturewith cooling in an ice bath
  2. stirringThe resulting suspension was stirred at ambient temperature under a nitrogen atmosphere overnight
  3. customThe reaction mixture was quenched with water (50 mL)
  4. extractionthen extracted with diethyl ether (150 mL)
  5. washThe organic layer was washed with water (5×50 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationthen concentrated

Sources & evidence

ORD record
ord-3b5ac8a5b1854f79944972dfbdf8fb6b
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Linked notes

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