Ethyl 4-(benzyloxy)-3-oxobutanoate → ethyl(S)-4-benzyloxy-3-hydroxybutyrate

300.0 g (1.27 moles) ethyl 4-benzyloxy-3-oxobutyrate, 300 ml ethanol, and 104.5 mg (0.127 mmol) [RuCl{(R)-segphos}]2(μ-Cl)3 [Me2NH2] were introduced in a nitrogen stream into a 1-L autoclave and flushed with hydrogen, and after introduction of hydrogen at a pressure of 1 MPa, the mixture was heated with stirring. The mixture was reacted at 90 to 95° C. for 7 hours. After the reaction solution was cooled to room temperature, the hydrogen was purged and replaced by nitrogen. The reaction solution was concentrated in a rotary evaporator and the residue was distilled under reduced pressure to give 263.3 g of the title compound (chemical purity, 96.2%; optical purity, 99.1% ee; and yield, 87%).

1. customflushed with hydrogen
2. temperatureafter introduction of hydrogen at a pressure of 1 MPa, the mixture was heated
3. customThe mixture was reacted at 90 to 95° C. for 7 hours
4. customthe hydrogen was purged
5. concentrationThe reaction solution was concentrated in a rotary evaporator
6. distillationthe residue was distilled under reduced pressure

ORD record

ord-6653db0ca57245e3b5cfcead20d36c84

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608214B2