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

HRID 2071023Notes

Reaction equation

HRID 2071023 reaction equation
[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]

Participants

5

Reactant 2

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5f0992afda0a4570b99e91d2630d0851
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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