Chlorotrimethylsilane → HCID 57475068, compound

HRID 1095580Notes

Reaction equation

HRID 1095580 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 (polar diastereomer) (124 mg, 0.3 mmol) was dissolved in ethyl acetate (50 ml). Me3SiCl (76 μl, 0.39 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 176 (100 mg, m.p. 173-176° C., 74%) 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-249b294151b3420b8f2011e75b750e16
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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