Tetrabutylammonium Fluoride → (4aR,8aS)-1-(1H-indol-6-yl)-3,3-dimethyldecahydroquinoxaline
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][C:20]1([CH3:49])[NH:29][C@H:28]2[C@H:23]([CH2:24][CH2:25][CH2:26][CH2:27]2)[N:22]([C:30]2[CH:38]=[C:37]3[C:33]([CH:34]=[CH:35][N:36]3[Si](C(C)C)(C(C)C)C(C)C)=[CH:32][CH:31]=2)[CH2:21]1>O1CCCC1>[NH:36]1[C:37]2[C:33](=[CH:32][CH:31]=[C:30]([N:22]3[C@@H:23]4[C@@H:28]([CH2:27][CH2:26][CH2:25][CH2:24]4)[NH:29][C:20]([CH3:49])([CH3:19])[CH2:21]3)[CH:38]=2)[CH:34]=[CH:35]1Participants
4
Procedure
Tetra-n-butyl ammonium fluoride (1 M in THF) (3.41 mL, 3.41 mol) was added to a tetrahydrofuran (15 mL) solution of (4aR,8aS)-3,3-dimethyl-1-(1-(triisopropylsilyl)-1H -indol-6-yl)decahydroquinoxaline (0.750 g, 1.71 mmol) with stirring at room temperature, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (ethyl acetate/hexane) to obtain a white solid. The obtained solid was recrystallized from diisopropyl ether/hexane to obtain (4aR,8aS)-1-(1H-indol-6-yl)-3,3-dimethyldecahydroquinoxaline (305 mg, yield: 63%).
Workup
- stirringthe mixture was stirred at room temperature for 1 hour
- distillationThe solvent was distilled off from the reaction mixture under reduced pressure
- customThe obtained residue was purified by NH-silica gel column chromatography (ethyl acetate/hexane)
- customto obtain a white solid
- customThe obtained solid was recrystallized from diisopropyl ether/hexane
Sources & evidence
- ORD record
- ord-2531858e92ce435a9fec63dbf99d9e53
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090572B2
Reaction notes
Loading…