Pyridine → HCID 54043483, Verbindung

HRID 1780510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1780510
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:23])([C:7]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:24].N1C=CC=CC=1.ClCCl.[C:34](Cl)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:23])([C:7]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[CH:17]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:24]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 62493Pivaloyl chlorideHCID 54238570HCID 54238570, Verbindung

Produkt 1

HCID 54043483HCID 54043483, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-(3-aminophenyl)-10b-methyl 1,2,3,4,4a,5,6,10b octahydrobenzo[f]quinolin-3-one (31 mg, 0.097 mmol), N,N-dimethylaminopyridine (3 mg, 0.024 mmol), 1 mL of pyridine and 0.5 mL of dichloromethane. The solution was cooled to 0°, and excess pivaloyl chloride (0.086 mL, 0.69 mmol) was added. The stirred mixture was allowed to warm to room temperature over 2 h. The mixture was diluted with chloroform, and washed with 5% aqueous hydrochloric acid solution, water, 5% queous sodium hydroxide solution, water, and the combined organic extracts were dried over sodium sulfate, concentrated and chromatographed on silica gel (ethyl acetate eluent) to give 25 mg (64%) of the title compound as a yellow solid. mp 95°-98°. FDMS m/e=404. α[D]589 =+62.50 (c=0.16, chloroform).

Aufarbeitung

  1. temperatureThe solution was cooled to 0°
  2. washwashed with 5% aqueous hydrochloric acid solution, water, 5% queous sodium hydroxide solution, water
  3. dry with materialthe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customchromatographed on silica gel (ethyl acetate eluent)

Quellen und Nachweise

ORD-Eintrag
ord-0ff2a4ef317e4285a2439768a4f94c0d
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05629007

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