Chlorotrimethylsilane → HCID 57475064, compound

HRID 1095573Notes

Reaction equation

HRID 1095573 reaction equation
[CH2:1]([C:8]1([N:29]([CH3:31])[CH3:30])[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si]([Cl:36])(C)(C)C>C(OCC)(=O)C>[ClH:36].[CH2:1]([C:8]1([N:29]([CH3:31])[CH3:30])[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 57475065HCID 57475065, compound

Product 1

HCID 57475064HCID 57475064, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(2-(4-Benzyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butanoic acid (260 mg, 0.6 mmol) was dissolved in ethyl acetate (50 ml). Me3SiCl (153 μl, 1.2 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 171 (197 mg, m.p. 90-93° C., 70%) was obtained as a white solid (purity <95%).

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-c7c7462819c64d71abfa17023785b793
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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