Methyl 3-oxovalerate → HCID 10149029, compound

Temperature

80 °C

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.

1. customAfter completion of the reaction
2. customthe solvent was removed by evaporation
3. additionTo the residue, toluene (500 mL) was added
4. stirringAfter the additions, the mixture was stirred at room temperature for 1 hour
5. filtrationthe precipitate was filtered off
6. customThe filtrate was evaporated
7. distillationthe residue was then distilled

ORD record

ord-cce6f8f75ce74e488be7e4e96c7b65b0

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07626034B2