Tetrahydrofuran → (+)-(4aR)-(10bR)-4-methyl-8-(1-acetyl-7-nitroindolin-5-yl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

HRID 1079222

Reaktionsgleichung

Reaktionsgleichung von HRID 1079222
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][C:11]=2[N+:13]([O-:15])=[O:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:17](=[O:20])([O-])[O-].[Na+].[Na+].[CH2:23]1[CH2:27]O[CH2:25][CH2:24]1>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:5][N:4]1[C@H:1]2[C@@:23]([CH3:27])([C:23]3[CH:27]=[CH:8][C:7]([C:9]4[CH:8]=[C:7]5[C:12](=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=4)[N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]5)=[CH:6][C:24]=3[CH2:25][CH2:2]2)[CH2:24][CH2:25][C:17]1=[O:20]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 27292431-Acetyl-5-bromo-7-nitroindoline

Produkt 1

HCID 54095089(+)-(4aR)-(10bR)-4-methyl-8-(1-acetyl-7-nitroindolin-5-yl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-oneAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one-8-boronic acid (178 mg, 0.65 mmol), tetrakis (triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), 1-acetyl-5-bromo-7-nitroindoline (185 mg, 0.65 mmol), 0.65 mL of 2M sodium carbonate and 2 mL of THF, fitted with a reflux condenser, and the stirred mixture was heated at 80°, under nitrogen, for 24 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2×25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (5% methanol/ethyl acetate eluent) to give 63 mg (22%) of the title compound a yellow solid. mp 235°-240°. FDMS: m/e=433. α[D]589 =+65.72 (c=0.99, chloroform).

Aufarbeitung

  1. customfitted with a reflux condenser
  2. temperaturethe stirred mixture was heated at 80°, under nitrogen, for 24 h
  3. temperatureThe mixture was cooled
  4. washwashed with brine (2×25 mL)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (5% methanol/ethyl acetate eluent)

Quellen und Nachweise

ORD-Eintrag
ord-1240f7a9e02e4fbbb53bd406070fe7bd
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05550134

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