Potassium Carbonate → 6-Benzyloxycarbonylamino-8-hydroxy-5,6,7,8-tetrahydroquinoline

HRID 1765330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765330
C([O:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH:7]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[CH2:19]([O:18][C:16]([NH:15][CH:7]1[CH2:6][CH:5]([OH:4])[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 211070758-Acetoxy-6-benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline

Produkt 1

HCID 211070736-Benzyloxycarbonylamino-8-hydroxy-5,6,7,8-tetrahydroquinolineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 8-acetoxy-6-benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline, cis-trans mixture (1.73 g, 5.07 mmol) in methanol (16 mL) at room temperature under nitrogen was added 10% aqueous potassium carbonate solution (8 mL, 5.79 mmol). After 24 h, the reaction mixture was diluted with methylene chloride. The organic layer was washed sequentially with saturated aqueous ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and evaporated under vacuum to obtain the title compound (1.47 g, 97%). Silica gel chromatography (eluted with 5% methanol in chloroform) provided inefficient separation of the cis and trans isomers. The cis isomer eluted first. Stereochemical assignment was made based on NOE experiments. Cis isomer: 13C NMR (400 MHz, CDCl3) δ 156.3, 155.8, 147.5, 138.0, 136.5, 128.5, 128.1, 123.1, 77.4, 67.5, 66.5, 44.4, 35.0. HPLC/MS [M+H]+, 299.

Aufarbeitung

  1. washThe organic layer was washed sequentially with saturated aqueous ammonium chloride solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b02e0bff0acf4a5999e12e3e89752451
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226942B2

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