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

HRID 75208

반응식

HRID 75208 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-4cc63b5c2c2540fda0eedca268d15367
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835423B2

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