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

HRID 503921ノート

反応式

HRID 503921 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f22e4a1567ea4a959e34c5a9adc7a720
出典データセット
uspto-grants-2010_08
特許番号
US07776910B2

反応ノート

読み込み中…