Chlorotrimethylsilane → HCID 24954348, compound

HRID 1095577Notes

Reaction equation

HRID 1095577 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18](O)[CH2:19][CH2:20][CH3:21])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1.[Si]([Cl:34])(C)(C)C.C(OCC)(=[O:37])C>>[ClH:34].[CH3:29][N:2]([CH3:1])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][CH2:20][CH2:21][OH:37])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8857Ethyl AcetateHCID 131729508HCID 131729508, compound

Product 1

HCID 24954348HCID 24954348, compound

Procedure

4-[(2-(4-Dimethylamino-4-phenylcyclohexyl)-1H-indol-3-yl)butan-1-ol (less polar diastereomer) (170 mg, 0.43 mmol) was dissolved in ethyl acetate (50 ml). Me3SiCl (108 μl, 0.86 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 173 (170 mg, m.p. 223-226° C., 91%) 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-30d3c05443a5409393502b34a5ea3761
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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