Methyl 3-oxo-3-phenylpropanoate → Methyl (3S)-3-hydroxy-3-phenylpropanoate
Reaction equation
[C:1]([CH2:9][C:10]([O:12][CH3:13])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO>[OH:8][C@H:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Into a 1-L autoclave was introduced methanol (360 mL) in a nitrogen stream. Then, [{RuCl((R)-SEGPHOS)}2(μ-Cl)3][Me2NH2] (82 mg: 0.1 mmol) and methyl benzoylacetate (178 g: 1.0 mol) were added. After hydrogen (4.0 MPa) was forced into the autoclave, the reaction mixture was heated to 80° C. and stirred for 5.5 hours to carry out asymmetric hydrogenation reaction. After cooling, methanol was removed from the reaction mixture, and the residue was distilled under reduced pressure (94-99° C./133 Pa) to obtain 170.6 g (yield, 95.3%) of methyl (S)-3-hydroxy-3-phenylpropionate. The asymmetric yield thereof was determined with the HPLC (CHIRALCEL OD-H, 4.6 mm×250 mm; hexane/isopropyl alcohol=95/5; flow rate, 1.0 mL/min; detection wavelength, UV-254 nm), and was found to be 97.2%.
Workup
- customhydrogenation reaction
- temperatureAfter cooling
- custommethanol was removed from the reaction mixture
- distillationthe residue was distilled under reduced pressure (94-99° C./133 Pa)
Sources & evidence
- ORD record
- ord-654ae020be1c412bbe9d2c2cf8d70e6e
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06492545B2
Reaction notes
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