Methyl iodide → HCID 66853289, compound

HRID 2060792Notes

Reaction equation

HRID 2060792 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:10]23[CH2:17][CH:16]([OH:18])[CH2:15][CH:14]2[CH2:13][O:12][N:11]3[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[CH:7]=[CH:8][CH:9]=1.[CH3:30]I>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([C:10]23[CH2:17][CH:16]([O:18][CH3:30])[CH2:15][CH:14]2[CH2:13][O:12][N:11]3[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 66853266HCID 66853266, compound

Product 1

HCID 66853289HCID 66853289, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.076 g, 1.89 mmol) is added to a 0° C. solution of racemic (3aRS,5RS,6aSR)-6a-(3-bromophenyl)-1-(2,4-dimethoxybenzyl)hexahydro-1H-cyclopenta[c]isoxazol-5-ol (0.684 g, 1.57 mmol) in DMF (7 mL). The reaction is warmed to room temperature for 10 minutes and then cooled to 0° C. Methyl iodide (0.246 g, 1.73 mmol) is added and the reaction is stirred at room temperature for 6 hours. Additional sodium hydride (0.032 g, 0.790 mmol) and methyl iodide (0.112 g, 0.790 mmol) is added and the reaction is stirred at room temperature for 18 hours. The reaction is quenched with water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the solvent is removed under reduced pressure. The resulting residue is purified by silica gel chromatography with 10% ethyl acetate in CH2Cl2 to give the title compound (0.443 g, 63%). ES/MS m/e (79Br/81Br) 448, 450 (M+1).

Workup

  1. temperaturecooled to 0° C
  2. stirringthe reaction is stirred at room temperature for 18 hours
  3. customThe reaction is quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure
  8. customThe resulting residue is purified by silica gel chromatography with 10% ethyl acetate in CH2Cl2

Sources & evidence

ORD record
ord-bc92130cb923451d8acc67f121f9c7c6
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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