Chlorotrimethylsilane → HCID 57475070, compound

HRID 1095582Notes

Reaction equation

HRID 1095582 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]([N:30]([CH3:32])[CH3:31])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)(=[O:3])[CH3:2].[Si]([Cl:37])(C)(C)C>C(OCC)(=O)C>[ClH:37].[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]([N:30]([CH3:32])[CH3:31])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:23]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 57475071HCID 57475071, compound

Product 1

HCID 57475070HCID 57475070, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(2-(4-(Dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)butyl acetate (non-polar diastereomer) (234 mg, 0.54 mmol) was dissolved in ethyl acetate (50 ml). Me3SiCl (136 μl, 1.08 mmol) was then added dropwise at RT. 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 178 (155 mg, m.p. 238-241° C., 61%, NMR purity <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 (2×5 ml)
  4. customdried
  5. customExample 178 (155 mg, m.p. 238-241° C., 61%, NMR purity <95%) was obtained as a white solid

Sources & evidence

ORD record
ord-3979eb89c54e4b8fa16f3067f70e1d6d
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…