Chlorotrimethylsilane → HCID 24953997, compound

HRID 1095588Notes

Reaction equation

HRID 1095588 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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][OH:21])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1.[Si]([Cl:33])(C)(C)C>C(OCC)(=O)C>[ClH:33].[CH3:28][N:2]([CH3:1])[C:3]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=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][OH:21])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 24953998HCID 24953998, compound

Product 1

HCID 24953997HCID 24953997, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(2-(4-(Dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propan-1-ol (non-polar diastereomer) (160 mg, 0.43 mmol) was dissolved in ethyl acetate (20 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 184 (159 mg, m.p. 248-250° C., 90%, 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 184 (159 mg, m.p. 248-250° C., 90%, NMR purity <95%) was obtained as a white solid

Sources & evidence

ORD record
ord-067d0589f3ff4eb480ab35bf9f069a76
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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