Vinyl Acetate → HCID 9920690, compound

One gram of 1-(3-trifluoromethylphenyl)-propan-2-ol, (±)-(1), is dissolved in 100 ml of hexane, then is added with 0.5 g of Novozym (lipase from Candida antarctica) and 1 ml of vinyl acetate. The suspension is then incubated at 45° C. in a rotating stirrer (300 rpm). After 1 h, when the reaction mixture contains only two compounds in 1:1 ratio, the reaction is stopped and the solvent is distilled off under vacuum. The resulting residue is subjected to chromatographic separation on silica gel, eluting with ethyl ether/petroleum ether gradient, to yield 0.627 g of (R)-1-(3-trifluoromethylphenyl)-propan-2-ol acetic ester, (−)-(2), (52% yield, 92% ee) and (S)-1-(3-trifluoromethylphenyl)-propan-2-ol, (+)-(1), 0.470 g (47% yield, >98% ee). The (−)-(2) ester is dissolved in 50 ml of hexane containing 1.5 ml of butanol and added with 0.5 g of Novozym. The suspension is then incubated at 45° C. in a rotating stirrer (300 rpm). After 5 h, the reaction is stopped to yield (R)-1-(3-trifluoromethylphenyl)-propan-2-ol, (−)-(1), 0.488 g (94% yield, >98% ee).

1. customThe suspension is then incubated at 45° C. in a rotating stirrer
2. distillationthe solvent is distilled off under vacuum
3. customThe resulting residue is subjected to chromatographic separation on silica gel
4. washeluting with ethyl ether/petroleum ether gradient

ORD record

ord-dd353fb7effc4f0089b3745e8047171e

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06987205B2