Chlorotrimethylsilane → HCID 24953999, compound

HRID 1095590Notes

Reaction equation

HRID 1095590 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 (less polar diastereomer) (190 mg, 0.51 mmol) was dissolved in ethyl acetate (50 ml). Me3SiCl (128 μl, 1.02 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 186 (120 mg, m.p. 217-220° C., 58%) was a white solid 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.68-2.03-(m, 10H), 2.37-2.47 (m, 1H), 2.54-2.62 (m, 6H), 2.68-2.78 (m, 2H), 2.98-3.11 (m, 1H), 3.12-3.22 (m, 2H), 3.93 (t, J=6.50, 6.50 Hz, 2H), 6.87-7.06 (m, 2H), 7.25 (d, J=7.80 Hz, 1H), 7.42 (d, J=7.80, 1 H) 7.48-7.60 (m, 3H), 7.67-7.82-(m, 2H), 10.00 (s, 1H), 11.34 (s, 1H)

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-d9207bcd166947049167f16bfa90c31a
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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