Sodium borohydride → (S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyronitrile

HRID 503921노트

반응식

HRID 503921 반응식
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([C:14](N2[C@@H](C(C)C)COC2=O)=[O:15])[CH2:11][C:12]#[N:13])=[C:6]([O:25][CH3:26])[CH:5]=1.OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O.C1COCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([CH2:14][OH:15])[CH2:11][C:12]#[N:13])=[C:6]([O:25][CH3:26])[CH:5]=1

참가 물질

6

반응물 3

HCID 4311764Sodium borohydrideHCID 66877211(S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrileHCID 86586342KHSO4 Na2SO4

생성물 1

HCID 66876540(S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyronitrile수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of sodium borohydride (389 mg) in water (1.82 mL) was added to a solution of (S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrile (749 mg, 1.895 mmol) in THF (6 mL) under nitrogen atmosphere. The mixture was stirred at room temperature for three hours. The reaction mixture was cooled to 0° C. and a solution of 10% KHSO4/Na2SO4 was carefully added. After the gas evolution stopped, the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 7/3) to give 470 mg (92% yield) of (S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyronitrile.

후처리

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc, 7/3)

출처 및 근거

ORD 기록
ord-f22e4a1567ea4a959e34c5a9adc7a720
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776910B2

반응 노트

불러오는 중…