Triacetoxyperiodinane → 6,11-Dihydro-5H-dipyrido[2,3-b:3',4'-f]azepin-5-one

HRID 75208

Reaktionsgleichung

Reaktionsgleichung von HRID 75208
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[N:23]1[C:28]2[NH:29][C:30]3[CH:38]=[CH:37][N:36]=[CH:35][C:31]=3[CH2:32][CH:33]([OH:34])[C:27]=2[CH:26]=[CH:25][CH:24]=1.S(=O)(=O)(O)[O-].[Na+]>ClCCl.O.C(=O)(O)[O-].[Na+]>[N:23]1[C:28]2[NH:29][C:30]3[CH:38]=[CH:37][N:36]=[CH:35][C:31]=3[CH2:32][C:33](=[O:34])[C:27]=2[CH:26]=[CH:25][CH:24]=1

Komponenten

7

Edukt 3

HCID 159087TriacetoxyperiodinaneHCID 516919Sodium BisulfateHCID 668863896,11-Dihydro-5H-dipyrido[2,3-b:3',4'-f]azepin-5-ol

Produkt 1

HCID 668868736,11-Dihydro-5H-dipyrido[2,3-b:3',4'-f]azepin-5-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Dess-Martin periodinane (0.810 g, 1.91 mmol) was added to a solution of 6,11-dihydro-5H-dipyrido[2,3-b:3′,4′-f]azepin-5-ol (0.370 g, 1.74 mmol, Intermediate D-5) in dichloromethane (30 mL) under an atmosphere of nitrogen and stirred for 1 h. The yellow mixture was poured into a solution of sodium bisulfate in water and stirred for 5 minutes. The mixture was then diluted with dichloromethane and sodium bicarbonate was added to adjust the pH to 8-9. The mixture was extracted three times with dichloromethane and the combined extracts were dried over sodium sulfate, filtered, and concentrated. The crude product residue was adsorbed onto silica gel and chromatographed on a silica gel column eluting with 10% methanol/dichloromethane to provide the desired product as a light tan solid (330 mg, 90%). 1H NMR (DMSO-d6): δ 10.55 (s, 1H), 8.51 (dd, 1H), 8.42 (s, 1H), 8.35 (d, 1H), 8.18 (dd, 1H), 7.33 (d, 1H), 7.06 (dd, 1H), 3.82 (s, 2H). LC/MS: 212 (M+H)+.

Aufarbeitung

  1. stirringstirred for 5 minutes
  2. additionwas added
  3. extractionThe mixture was extracted three times with dichloromethane
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on a silica gel column
  8. washeluting with 10% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-4cc63b5c2c2540fda0eedca268d15367
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835423B2

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