Methyl iodide → HCID 10665341, compound

HRID 1779960Notes

Reaction equation

HRID 1779960 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16]2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:27]I>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16]2)=[CH:11][CH:10]=1)[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22370507HCID 22370507, compound

Product 1

HCID 10665341HCID 10665341, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of N,N-dimethylformamide, 0.67 g of ethyl 7-[N-(t-butoxycarbonyl)amino]-1,2,3,4-tetrahydro-naphthalene-2-acetate was dissolved and 0.096 g of 60% sodium hydride was added under cooling and stirred for 5 minutes at room temperature. To the mixture, 0.57 g of methyl iodide was dropwise added and allowed to stand overnight at room temperature. The reaction mixture was concentrated under reduced pressure and the concentrated residue was extracted with ethyl acetate. The ethyl acetate solution was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, then the obtained crude product was purified by silica gel column chromatography using a mixture, ethyl acetate:n-hexane=1:10, as a developer to give 0.67 g of ethyl 7-[N-(t-butoxycarbonyl)-N-methylamino]-1,2,3,4-tetrahydronaphthalene-2-acetate.

Workup

  1. temperatureunder cooling
  2. waitto stand overnight at room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionthe concentrated residue was extracted with ethyl acetate
  5. dry with materialThe ethyl acetate solution was dried with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained crude product
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b417abbdaf2e4233b606242835b8037e
Source dataset
uspto-grants-1997_05
Patent number
US05629321

Reaction notes

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