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

HRID 627242ノート

反応式

HRID 627242 の反応式
[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

参加物

5

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 89851393(R)-tert-butyl 4-(cyclopropyl(hydroxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-aaf102eb16724a6e9b4aa81ec41f9942
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

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