Triacetoxyperiodinane → (R)-tert-butyl 4-(cyclopropanecarbonyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 627242노트

반응식

HRID 627242 반응식
[CH:1]1([CH:4]([OH:19])[C@H:5]2[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(OCC)(=O)C>[CH:1]1([C:4]([C@H:5]2[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:19])[CH2:2][CH2:3]1

참가 물질

5

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 89851393(R)-tert-butyl 4-(cyclopropyl(hydroxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate2회

생성물 1

HCID 89851368(R)-tert-butyl 4-(cyclopropanecarbonyl)-2,2-dimethyloxazolidine-3-carboxylate수율 90.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (R)-tert-butyl 4-(cyclopropyl(hydroxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate (Intermediate 230, 12.47 g, 45.95 mmol) in DCM (300 mL) at room temperature was added Dess-Martin periodinane (29.2 g, 68.93 mmol). The reaction mixture was stirred overnight then diluted with ethyl acetate and washed with saturated sodium bicarbonate. An emulsion formed and was filtered through celite. The layers were separated and the organics washed with brine. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the title compound as a colorless oil (11.15 g, 90%).

후처리

  1. washwashed with saturated sodium bicarbonate
  2. customAn emulsion formed
  3. filtrationwas filtered through celite
  4. customThe layers were separated
  5. washthe organics washed with brine
  6. dry with materialThe organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-aaf102eb16724a6e9b4aa81ec41f9942
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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