3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → (R)-tert-butyl 4-(cyclopropyl(hydroxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 627241ノート

反応式

HRID 627241 の反応式
[CH:1]([C@H:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:2].[CH:17]1([Mg]Br)[CH2:19][CH2:18]1>C1COCC1>[CH:17]1([CH:1]([OH:2])[C@H:3]2[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:19][CH2:18]1

参加物

4

反応物 2

HCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 178418630HCID 178418630、化合物

生成物 1

HCID 89851393(R)-tert-butyl 4-(cyclopropyl(hydroxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (R)-tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate (Aldrich, 12.44 g, 54.26 mmol) in THF (150 mL) at −78° C. was added cyclopropylmagnesium bromide (217 mL, 108.52 mmol) dropwise. The reaction mixture was allowed to warm to room temperature and stir overnight. The reaction was quenched with water and diluted with ethyl acetate and brine. The resulting emulsion was filtered through celite and the layers separated. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the title compound as a light yellow oil (12.47 g, 85%).

後処理

  1. customThe reaction was quenched with water
  2. additiondiluted with ethyl acetate and brine
  3. filtrationThe resulting emulsion was filtered through celite
  4. customthe layers separated
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-1276d42fd0f24889a2b7195583168085
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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