Chlorotrimethylsilane → HCID 24953999, compound

HRID 1095589Notes

Reaction equation

HRID 1095589 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[CH:17]1[CH2:22][CH2:21][C:20]([N:29]([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)(=[O:3])[CH3:2].[Si]([Cl:36])(C)(C)C>C(OCC)(=O)C>[ClH:36].[C:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[CH:17]1[CH2:22][CH2:21][C:20]([N:29]([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 24954000HCID 24954000, compound

Product 1

HCID 24953999HCID 24953999, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(2-(4-(Dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propyl acetate (more polar diastereomer) (60 mg, 0.16 mmol) was dissolved in ethyl acetate (20 ml). Me3SiCl (40 μl, 0.32 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 (1×5 ml) and then dried. Example 185 (55 mg, m.p. 229-232° C., 84%) was a white solid.

Workup

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

Sources & evidence

ORD record
ord-4617733a45a84d889393989bbd6d3a8b
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…