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

HRID 1528294노트

반응식

HRID 1528294 반응식
[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

참가 물질

10

반응물 4

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

생성물 1

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

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매HCID 44558591Tri-t-butylphosphine fluoroborate촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ec513ae83d8743e0a2a0ca7f97ba55db
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090572B2

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