Chlorotrimethylsilane → HCID 24954346, compound

HRID 1095578Notes

Reaction equation

HRID 1095578 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 (less polar diastereomer) (120 mg, 0.27 mmol) was dissolved in ethyl acetate (10 ml), and Me3SiCl (68 μl, 0.54 mmol) was 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 174 (117 mg, m.p. 187-191° 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-7902a2f0ea254a0480c7bd82ec47e913
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…