Methyl 3-oxovalerate → HCID 10149029, compound

Participants

Reaction Conditions

Reaction Steps

Ru(OAc)2((R)-dm-segphos) (1.21 g, 1.28 mmol), methyl 3-oxopentanoate (50.0 g, 384 mmol), ammonium acetate (29.6 g, 384 mmol) and methanol (500 mL) were placed in a 1 L stainless steel autoclave under nitrogen atmosphere, and then the mixture was stirred under a hydrogen pressure of 3 MPa at 80° C. for 16 hours. After completion of the reaction, the solvent was removed by evaporation. To the residue, toluene (500 mL) was added, and then a 28% solution of sodium methoxide in methanol (66.7 g, 346 mmol) was added at room temperature. After the additions, the mixture was stirred at room temperature for 1 hour, and then the precipitate was filtered off. The filtrate was evaporated and the residue was then distilled to give methyl (3R)-3-aminopentanoate (32.0 g, colorless oil) in 63.5% yield. The enantiomeric excess of the product obtained above was determined to be 98.4% ee by HPLC analysis using a CHIRALCEL OD-H column after conversion into methyl (3R)-3-(4-nitrobenzoylamino)pentanoate.

Provenance & Evidence