Methyl iodide → HCID 66783138, compound

HRID 1096261Notes

Reaction equation

HRID 1096261 reaction equation
[H-].[Na+].[C:3]([Si:7]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[O:8][CH2:9][CH2:10][CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH:16]([CH3:30])[C:15]1=[O:31])[CH2:12][OH:13])([CH3:6])([CH3:5])[CH3:4].I[CH3:45]>CN(C)C=O>[C:3]([Si:7]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[O:8][CH2:9][CH2:10][CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:29])[F:28])[CH:21]=2)[CH:16]([CH3:30])[C:15]1=[O:31])[CH2:12][O:13][CH3:45])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66783140HCID 66783140, compound

Product 1

HCID 66783138HCID 66783138, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (55% dispersion in mineral oil, 20 mg, 0.45 mmol) was added at 0° C. to a solution of 1-[3-(tert-butyl-diphenyl-silanyloxy)-1-hydroxymethyl-propyl]-3-methyl-4-(3-trifluoromethyl-phenyl)-piperazin-2-one (224 mg, 0.38 mmol) in N,N-dimethylformamide (3.5 mL), then after 5 min a solution of iodomethane (54 mg, 0.45 mmol) in N,N-dimethylformamide (1.5 mL) was added, then after 3 h the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 19:1) afforded the title compound (139 mg, 61%). Light yellow oil, MS: 599.3 (M+H)+.

Workup

  1. customafter 3 h the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f9eb6647fbfd460da49c9d1a842a7ec5
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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