Vinyl Acetate → HCID 86604660, compound

HRID 1391776Notes

Reaction equation

HRID 1391776 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1.[C:14](OC=C)(=[O:16])[CH3:15]>C1CCCCC1>[C:14]([O:13][C@@H:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)[CH2:9][CH2:10][CH2:11][CH3:12])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 586299071-(6-Bromo-2-pyridinyl)-1-pentanol

Product 1

HCID 86604660HCID 86604660, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

To a gently shaking solution of 1-(6-bromo-2-pyridinyl)-1-pentanol (1.00 g, 4.10 mmol) in dry cyclohexane (100 mL) was added Lipase PS-C “Amano” (Pseudomonas cepacia) (9.97 g) followed by vinyl acetate (1.5 mL, 16.27 mmol). Shaking was continued for 7.5 h with continual monitoring by chiral HPLC. The mixture was then filtered and the filtrate reduced under vacuum to give an oil which was purified by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (gradient 50:1 to 2:1) to afford (1R)-1-(6-bromo-2-pyridinyl)pentyl acetate as an oil (737 mg, 63%). LC/MS: m/z 286.1/288.1 [M+H]+, Rt 3.38 min. Analytical chiral HPLC (25 cm Chiralpak AD) eluting with 2% EtOH in heptane, f=1.0 mL/min, wavelength 215 nm, (S-) Rt 5.1 min and (R-) Rt 5.4 min (43% ee) and the title compound as an oil (349 mg).

Workup

  1. filtrationThe mixture was then filtered
  2. customto give an oil which
  3. customwas purified by SPE (silica, 20 g cartridge)
  4. washeluting with cyclohexane

Sources & evidence

ORD record
ord-c0d3aa33535348d48d5b67254ac29b5a
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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