Methyl iodide → HCID 70188013, compound

HRID 344061Notes

Reaction equation

HRID 344061 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH2:7][O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH:13]([CH2:19][NH:20][C:21](=[O:36])[O:22][CH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:14]2)=[O:6].[CH3:37]I>CN(C)C=O>[CH3:37][N:20]([CH2:19][CH:13]1[CH2:12][CH2:11][C:10]2[C:15](=[CH:16][CH:17]=[CH:18][C:9]=2[O:8][CH2:7][C:5]([O:4][CH3:3])=[O:6])[CH2:14]1)[C:21](=[O:36])[O:22][CH:23]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 70187837HCID 70187837, compound

Product 1

HCID 70188013HCID 70188013, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Sodium hydride (10.2 mg) was added to a stirred solution of benzhydryl N-[[1,2,3,4-tetrahydro-5-(methoxycarbonylmethoxy)-2-naphthyl]methyl]carbamate (117 mg) and methyl iodide (36 mg) in N,N-dimethylformamide (1.2 ml) under ice cooling and the mixture was stirred at the same temperature for 7 hours, then another 60% sodium hydride (10.2 mg) and methyl iodide (36 mg) was added thereto. The resulting mixture was stirred at room temperature for 3 days and extracted with ethyl acetate. The extract was washed twice with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (toluene-ethyl acetate) over silica gel to afford benzhydryl N-methyl-N-[[1,2,3,4-tetrahydro-5-(methoxycarbonylmethoxy)-2-naphthyl]methyl]carbamate (71 mg) as an oil.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 3 days
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed twice with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed (toluene-ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-33e94510668b4a548371d04a9a6f122c
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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