Cyclooctanecarbaldehyde → HCID 10765199, Verbindung

HRID 370269

Reaktionsgleichung

Reaktionsgleichung von HRID 370269
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([CH:11]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:18][C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:10])[CH2:4][CH2:3]1.[CH:25]1([CH:33]=O)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH:25]1([CH2:33][N:2]2[CH2:3][CH2:4][CH:5]([NH:8][C:9]([CH:11]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[O:18][C:19]4[C:24]3=[CH:23][CH:22]=[CH:21][CH:20]=4)=[O:10])[CH2:6][CH2:7]2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Komponenten

6

Edukt 4

HCID 81190CyclooctanecarbaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23283003N-(piperidin-4-yl)xanthene-9-carboxamide hydrochloride

Produkt 1

HCID 10765199HCID 10765199, VerbindungAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.16 g of N-(piperidin-4-yl)xanthene-9-carboxamide hydrochloride and 586 mg of cyclooctanecarbaldehyde were suspended in 60 ml of tetrahydrofuran at room temperature, and 1.60 g of sodium triacetoxyborohydride was added thereto, followed by stirring for 12 hours at the same temperature. Saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography (developing solvent: chloroform--chloroform/methanol=50/1), and 660 mg of the title compound as a white solid was obtained.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialby drying over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (developing solvent: chloroform--chloroform/methanol=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-9d8f9799d59b4fccaab715570a02b422
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140338

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