Methyl 3-oxovalerate → Methyl (S)-3-hydroxypentanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 6.22 mg (48 mmol) of methyl 3-ketovalerate in 48 ml methanol, 36 mg (0.004 mmol) RuCl2(S)-binap was added and stirred in an autoclave under a hydrogen pressure of 30 atm at 80° C. for 66 hours. After concentration and distillation, 5.71 g (43.2 mmol, 97% ee) of methyl (S)-3-hydroxyvalerate was obtained. The condition of chiral HPLC is the following. Column, CHIRALPAK OD manufactured by Daicel Chemical Industries, Ltd.; Eluate, Hexane:2-propanol=95:5; flow rate, 1.0 mL/min; Wavelength of detection, 210 nm; Temperature, 25° C.; Retention time, 15 min (R) and 27 min (S).

Provenance & Evidence