Vinyl Acetate → (R)-1-(5-bromopyridin-3-yl)ethyl acetate

HRID 2071023ノート

反応式

HRID 2071023 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:5]=[N:6][CH:7]=1.[C:11]([O:14][CH:15]=[CH2:16])(=[O:13])[CH3:12]>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:10])[CH3:9])[CH:5]=[N:6][CH:7]=1.[C:11]([O:14][C@@H:15]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH3:16])(=[O:13])[CH3:12]

参加物

5

反応物 2

HCID 7904Vinyl AcetateHCID 129974353-Bromo-5-(1-hydroxyethyl)pyridine

生成物 2

HCID 68669858(R)-1-(5-bromopyridin-3-yl)ethyl acetateHCID 68671332(S)-1-(5-bromopyridin-3-yl)ethan-1-ol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a stirred solution of 1-(5-bromopyridin-3-yl)ethanol (2.0 g) in anhydrous Et2O (50 mL) at 0° C., was vinyl acetate (2 mL), 4A° molecular sieves (2.0 g), Lipase immobilized from Candida Antarctica (200 mg) and the reaction was stirred for 16 h. The catalyst and molecular sieves were filtered off and the solvent was concentrated under reduced pressure. The residue was purified by column chromatography (30% EtOAc in hexanes) to provide 1.0 g of (S)-1-(5-bromopyridin-3-yl)ethanol and 1.18 g of (R)-1-(5-bromopyridin-3-yl)ethyl acetate.

後処理

  1. customat 0° C.
  2. filtrationThe catalyst and molecular sieves were filtered off
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-5f0992afda0a4570b99e91d2630d0851
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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