Chlorotrimethylsilane → HCID 24954346, compound

HRID 1095579Notes

Reaction equation

HRID 1095579 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]=1[CH:18]1[CH2:23][CH2:22][C:21]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([N:24]([CH3:26])[CH3:25])[CH2:20][CH2:19]1)(=[O:3])[CH3:2].[Si]([Cl:38])(C)(C)C>C(OCC)(=O)C>[ClH:38].[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]=1[CH:18]1[CH2:19][CH2:20][C:21]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([N:24]([CH3:26])[CH3:25])[CH2:22][CH2:23]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 24954347HCID 24954347, compound

Product 1

HCID 24954346HCID 24954346, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(2-(4-Benzyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butyl acetate (more polar diastereomer) (87 mg, 0.19 mmol) was dissolved in ethyl acetate (7 ml). Me3SiCl (49 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 175 (85 mg, m.p. 194-197° C., 90%) 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-0d5186a4e4c34b0cba3566face024efc
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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