Ethyl 4-(benzyloxy)-3-oxobutanoate → Ethyl (R)-4-benzyloxy-3-hydroxybutyrate

Participants

Reaction Steps

300.0 g (1.27 moles) ethyl 4-benzyloxy-3-oxobutyrate, 300 ml ethanol, and 104.5 mg (0.127 mmol) [RuCl{(S)-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 265.1 g of the title compound (chemical purity, 95.5%; optical purity, 99.1% ee; and yield, 87.6%).

Provenance & Evidence