Methyl iodide → HCID 53897392, compound

HRID 987063Notes

Reaction equation

HRID 987063 reaction equation
[CH3:1][CH:2]1[CH:11]=[C:10]2[CH:5]([CH:6]([CH2:13][CH2:14][C:15]3[NH:16][C:17](=[O:21])[CH:18]=[CH:19][CH:20]=3)[CH:7]([CH3:12])[CH:8]=[CH:9]2)[CH:4]([O:22][C:23](=[O:28])[CH:24]([CH3:27])[CH2:25][CH3:26])[CH2:3]1.[C:29](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:1][CH:2]1[CH:11]=[C:10]2[CH:5]([CH:6]([CH2:13][CH2:14][C:15]3[N:16]([CH3:29])[C:17](=[O:21])[CH:18]=[CH:19][CH:20]=3)[CH:7]([CH3:12])[CH:8]=[CH:9]2)[CH:4]([O:22][C:23](=[O:28])[CH:24]([CH3:27])[CH2:25][CH3:26])[CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 53852540HCID 53852540, compound

Product 1

HCID 53897392HCID 53897392, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 77 mg (0.2 mmol) 2-methyl-butyric acid 3,7-dimethyl-8-[2-(6-oxo-1,6-dihydro-pyridin-2-yl)-ethyl]-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester in 5 ml DMF are added 0.1 g (0.8 mmol) potassium carbonate and 0.1 g (0.8 mmol) methyl iodide. After 2 hours at room temperature the mixture is poured on water. The aqueous phase is separated and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is evaporated in vacuo. The residue is chromatographed over silica gel eluting with hexane/acetone 1/1 to afford the title compound as white powder.

Workup

  1. additionAfter 2 hours at room temperature the mixture is poured on water
  2. customThe aqueous phase is separated
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is evaporated in vacuo
  6. customThe residue is chromatographed over silica gel eluting with hexane/acetone 1/1

Sources & evidence

ORD record
ord-5eb9445b251d41f892801edf5e01a123
Source dataset
uspto-grants-2003_10
Patent number
US06630492B1

Reaction notes

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