Chlorotrimethylsilane → HCID 57475068, compound

HRID 1095581Notes

Reaction equation

HRID 1095581 reaction equation
[CH2:1]([C:5]1([N:28]([CH3:30])[CH3:29])[CH2:10][CH2:9][CH:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25](=[O:27])[CH3:26])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[Si]([Cl:35])(C)(C)C>C(OCC)(=O)C>[ClH:35].[C:25]([O:24][CH2:23][CH2:22][CH2:21][CH2:20][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[CH:8]1[CH2:9][CH2:10][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])([N:28]([CH3:30])[CH3:29])[CH2:6][CH2:7]1)(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 57475069HCID 57475069, compound

Product 1

HCID 57475068HCID 57475068, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid 4-[2-(4-butyl-4-dimethylaminocyclohexyl)-1H-indol-3-yl]butyl ester (non-polar diastereomer) (206 mg, 0.5 mmol) was dissolved in ethyl acetate (50 ml). Me3SiCl (126 μl, 1 mmol) was then added dropwise at RT and the mixture was stirred for 1 h. A white precipitate precipitated out. The precipitate was filtered off with suction, washed with ethyl acetate (2×5 ml) and then dried. Example 177 (150 mg, m.p. 128-131° C., 67%) was obtained as a white solid

Workup

  1. customA white precipitate precipitated out
  2. filtrationThe precipitate was filtered off with suction
  3. washwashed with ethyl acetate (2×5 ml)
  4. customdried

Sources & evidence

ORD record
ord-55a7adad828e47fe9b336305c8b897bd
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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