Trimethylsilyl triflate → N,N-dimethyl-4-phenyl-5',7',8',9'-tetrahydrospiro[cyclohexane-1,6'-pyrido[4,3-b]indole]-4-amine
Reaction equation
C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[CH3:13][N:14]([CH3:40])[C:15]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:20][CH2:19][C:18]([CH2:22][CH2:23][CH2:24][C:25]2[C:29]3[CH:30]=[N:31][CH:32]=[CH:33][C:28]=3[NH:27][CH:26]=2)(O)[CH2:17][CH2:16]1>ClCCl>[CH3:13][N:14]([CH3:40])[C:15]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:20][CH2:19][C:18]2([C:26]3[NH:27][C:28]4[CH:33]=[CH:32][N:31]=[CH:30][C:29]=4[C:25]=3[CH2:24][CH2:23][CH2:22]2)[CH2:17][CH2:16]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoromethane sulphonic acid trimethylsilyl ester (409 mg, 334 μL, 1.84 mmol) was added to a solution of 4-dimethylamino-4-phenyl-1-[3-(1H-pyrrolo[3,2-c]pyridin-3-yl)propyl]-cyclohexanol (172 mg, 0.39 mmol) in anhydrous dichloromethane (30 mL) and stirred for 10 d at room temperature. The reaction mixture was then diluted with dichloromethane (10 mL), firstly washed with 1 N sodium carbonate solution (2×10 mL) and then with water and saturated sodium chloride solution (10 mL each), dried with sodium sulphate and concentrated to low volume in a vacuum. The residue (131 mg) was taken up in methanol (15 mL) and stirred overnight at room temperature and then concentrated to low volume in a vacuum.
Workup
- washfirstly washed with 1 N sodium carbonate solution (2×10 mL)
- dry with materialwith water and saturated sodium chloride solution (10 mL each), dried with sodium sulphate
- concentrationconcentrated to low volume in a vacuum
- stirringstirred overnight at room temperature
- concentrationconcentrated to low volume in a vacuum
Sources & evidence
- ORD record
- ord-8e86a06a8ba9410582f06ea0c3ba1fb1
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288430B2
Reaction notes
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