Chlorotrimethylsilane → HCID 10345215, compound

HRID 2357476Notes

Reaction equation

HRID 2357476 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[CH2:13]2)=[O:11])[CH2:5][CH2:4]1.C[Si](C)(C)[Cl:36]>CC(CC)=O>[ClH:36].[CH3:33][N:2]([CH3:1])[C:3]1([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[CH2:13]2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 103452162-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone

Product 1

HCID 10345215HCID 10345215, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone (329 mg, 0.73 mmole) was dissolved in ethyl methyl ketone (10 ml) and trimethylchlorosilane (0.14 ml, 1.1 mmole) was added, and the whole was stirred for 1.5 hours at RT. The precipitated hydrochloride was isolated in a yield of 93% (329 mg) and had an m.p. of 170°-177° C. (Example 41).

Sources & evidence

ORD record
ord-04675c1e51e341bfa472b72f82349792
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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