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

HRID 627241노트

반응식

HRID 627241 반응식
[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

참가 물질

4

반응물 2

HCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 178418630HCID 178418630, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1276d42fd0f24889a2b7195583168085
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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