Chlorotrimethylsilane → HCID 24953995, compound

HRID 1095584Notes

Reaction equation

HRID 1095584 reaction equation
[CH2:1]([C:5]1([N:24]([CH3:26])[CH3:25])[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][OH:23])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[Si]([Cl:31])(C)(C)C>C(OCC)(=O)C>[ClH:31].[CH2:1]([C:5]1([N:24]([CH3:26])[CH3:25])[CH2:6][CH2:7][CH:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH2:20][CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 24953996HCID 24953996, compound

Product 1

HCID 24953995HCID 24953995, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(2-(4-Butyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)propan-1-ol (more polar diastereomer) (54 mg, 0.15 mmol) was dissolved in ethyl acetate (5 ml). Me3SiCl (38 μl, 0.3 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 (2×3 ml) and then dried. Example 181 (57 mg, m.p. 128-132° C., 95%) 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 (2×3 ml)
  4. customdried

Sources & evidence

ORD record
ord-4e08aeead440455e97488c12ce310607
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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