Methyl iodide → HCID 19980408, compound

HRID 1461341Notes

Reaction equation

HRID 1461341 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:16][CH2:15][C:9]2([O:13][CH2:12][CH:11]([OH:14])[CH2:10]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].[CH3:19]I>C1COCC1.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][C:9]2([O:13][CH2:12][CH:11]([O:14][CH3:19])[CH2:10]2)[CH2:15][CH2:16]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 10398927HCID 10398927, compound

Product 1

HCID 19980408HCID 19980408, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

8-Ethoxycarbonyl-3-hydroxy-1-oxa-8-azaspiro[4.5]decane (1 g, 0.0044 mol) was dissolved in anhydrous THF (40 ml) under nitrogen and cooled with an ice-bath. Sodium hydride (0.22 g, 5.5 mmol as a 60% oil dispersion) was added and the reaction was stirred at 0° C. for 20 minutes. Methyl iodide (2.0 g, 0.9 ml) in THF (10 ml) was added dropwise. The reaction was allowed to warm to room temperature and stirred for 3 hours. An additional 0.9 ml of methyl iodide was added at 0° C. and stirring was continued overnight. The cooled reaction was diluted with water (10 ml). The aqueous THF was washed with saturated brine and dried over Na2SO4. The solvents were evaporated and the residue was purified by flash chromatography on silica gel by elution with ammoniated 2% methanol/chloroform. Evaporation of the solvents gave 0.97 g of a pale orange oil.

Workup

  1. temperaturecooled with an ice-bath
  2. temperatureto warm to room temperature
  3. stirringstirred for 3 hours
  4. stirringstirring
  5. waitwas continued overnight
  6. customThe cooled reaction
  7. washThe aqueous THF was washed with saturated brine
  8. dry with materialdried over Na2SO4
  9. customThe solvents were evaporated
  10. customthe residue was purified by flash chromatography on silica gel by elution with ammoniated 2% methanol/chloroform
  11. customEvaporation of the solvents

Sources & evidence

ORD record
ord-d76fee9250bb452eaf58e71fc2bab23f
Source dataset
uspto-grants-1991_12
Patent number
US05075317

Reaction notes

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