Methyl iodide → Benzyl methyl4-oxocyclohexylcarbamate

HRID 1896859Notes

Reaction equation

HRID 1896859 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.[CH3:19][Si](C)(C)[N-][Si](C)(C)C.[Li+].IC>CN(C=O)C>[CH3:19][N:8]([CH:5]1[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]1)[C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 14615292Benzyl (4-oxocyclohexyl)carbamate

Product 1

HCID 58562802Benzyl methyl4-oxocyclohexylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl (4-oxocyclohexyl)carbamate (500 mg, 2.0 mmol) in DMF was treated with lithium hexamethyldisilazid (2.0 mmol) at room temperature. This solution was stirred for 30 min and was then treated with iodomethane (0.25 mL, 4.0 mmol) and stirred for 18 h. DMF was removed under vacuum and the residue was purified by silica column chromatography to give the title compound.

Workup

  1. stirringstirred for 18 h
  2. customDMF was removed under vacuum
  3. customthe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-74e4d7bc9cd1415cba6d13b674ad708b
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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