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

HRID 1528294ノート

反応式

HRID 1528294 の反応式
[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

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 167845palladium(II) acetate触媒HCID 44558591Tri-t-butylphosphine fluoroborate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ec513ae83d8743e0a2a0ca7f97ba55db
出典データセット
uspto-grants-2015_07
特許番号
US09090572B2

反応ノート

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