Methyl 3-oxovalerate → Methyl (S)-3-hydroxypentanoate
Reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5]>CO>[OH:1][C@@H:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
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).
Workup
- concentrationAfter concentration and distillation
Sources & evidence
- ORD record
- ord-fd977c8e2a464afc8b7fac7f44d2c62c
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07145030B2
Reaction notes
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