Sulfuric acid magnesium salt (1:1) → (4aR,8aS)-3,3-dimethyl-1-(1-(triisopropylsilyl)-1H-indol-6-yl)decahydroquinoxaline

HRID 1528294Notes

Reaction equation

HRID 1528294 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:11][NH:10][C@@H:9]2[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:3]1.Br[C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[CH:19][N:20]2[Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])=[CH:16][CH:15]=1.CC(C)([O-])C.[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[NH:3][C@H:4]2[C@H:9]([CH2:8][CH2:7][CH2:6][CH2:5]2)[N:10]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[CH:19][N:20]3[Si:23]([CH:27]([CH3:29])[CH3:28])([CH:30]([CH3:32])[CH3:31])[CH:24]([CH3:25])[CH3:26])=[CH:16][CH:15]=2)[CH2:11]1

Participants

10

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 129912436-bromo-1-(triisopropylsilyl)-1H-indoleHCID 23676156Sodium t-butoxideHCID 66800071(4aS,8aR)-2,2-dimethyldecahydroquinoxaline

Product 1

HCID 66803274(4aR,8aS)-3,3-dimethyl-1-(1-(triisopropylsilyl)-1H-indol-6-yl)decahydroquinoxalineYield 85.3%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 44558591Tri-t-butylphosphine fluoroborateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A toluene (8 mL) suspension of (4aS,8aR)-2,2-dimethyldecahydroquinoxaline (337 mg, 2.00 mmol), 6-bromo-1-(triisopropylsilyl)-1H-indole (846 mg, 2.40 mmol), sodium tert-butoxide (269 mg, 2.80 mmol), palladium (II) acetate (22.5 mg, 0.0902 mmol), and tri-tert -butylphosphine tetrafluoroborate (29.1 mg, 0.101 mmol) was stirred for 5 hours under reflux in a nitrogen atmosphere. The reaction mixture was cooled to room temperature. Then, water (0.5 mL) and ethyl acetate (10 mL) were added thereto, and the mixture was stirred, followed by addition of magnesium sulfate. Insoluble matter was filtered through celite, and the filtrate was then concentrated under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (n-hexane:ethyl acetate) to obtain colorless, amorphous (4aR,8aS)-3,3-dimethyl-1-(1-(triisopropylsilyl)-1H-indol-6-yl)decahydroquinoxaline (0.75 g, yield; 85%).

Workup

  1. temperatureunder reflux in a nitrogen atmosphere
  2. stirringthe mixture was stirred
  3. filtrationInsoluble matter was filtered through celite
  4. concentrationthe filtrate was then concentrated under reduced pressure
  5. customThe obtained residue was purified by NH-silica gel column chromatography (n-hexane:ethyl acetate)
  6. customto obtain colorless

Sources & evidence

ORD record
ord-ec513ae83d8743e0a2a0ca7f97ba55db
Source dataset
uspto-grants-2015_07
Patent number
US09090572B2

Reaction notes

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