Methyl iodide → Benzyl methyl4-oxocyclohexylcarbamate

HRID 2175542Notes

Reaction equation

HRID 2175542 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-a796961bd7cd46e7b2cd14f3942d1cc9
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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