Methyl 3-oxohexanoate → methyl (S)-3-hydroxyhexanoate
Reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][CH3:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5]>CO>[OH:1][C@@H:2]([CH2:8][CH2:9][CH3:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
To a solution of 2.88 g (20 mmol) of methyl 3-ketohexanoate in 10 ml methanol, 36 mg (0.004 mmol) RuCl2(R)-binap was added and stirred in an autoclave under a hydrogen pressure of 100 atm at 30° C. for 66 hours. After concentration and distillation, 2.24 g (15.4 mmol, 99% ee) of methyl (S)-3-hydroxyhexanoate was obtained. The condition of chiral HPLC is the following. Column, CHIRALPAK OD-H manufactured by Daicel Chemical Industries, Ltd.; Eluate, Hexane:2-propanol=90:10; flow rate, 1.0 mL/min; Wavelength of detection, 210 nm; Temperature, 25° C.; Retention time, 5 min (R) and 7 min (S).
Workup
- concentrationAfter concentration and distillation
Sources & evidence
- ORD record
- ord-edc8082fb3da443abed3d7bad5c313d4
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07145030B2
Reaction notes
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