Acetic Acid → HCID 13416927, compound

Temperature

80 °C

Ru(OCOCH3)2((R)-dm-binap)(20.5 mg, 0.0215 mmol), methyl acetoacetate (500 mg, 4.305 mmol), benzylamine (461 mg, 4.305 mmol) and methanol (2.5 mL) were placed in a 2.5 mL-stainless autoclave under atmosphere of nitrogen, and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was cooled down to room temperature, and acetic acid (259 mg, 4.305 mmol) was added thereto. The mixture was further stirred under a hydrogen pressure of 3 MPa at 80° C. for 15 hours. After completion of the reaction, the solvent was removed by evaporation in vacuo, and the residue was purified by column chromatography on silica gel (eluent:hexane ethyl acetate/triethylamine=75/25/5) to give the objective methyl (−)-3-(benzylamino)butanoate (141 mg) as a colorless oil in 15.8% yield. The enantiomeric excess of the resulting methyl (−)-3-(benzylamino)butanoate was determined to be 44.5% ee by HPLC analysis using a CHIRALCEL OD-H column.

1. temperatureThe reaction mixture was cooled down to room temperature
2. stirringThe mixture was further stirred under a hydrogen pressure of 3 MPa at 80° C. for 15 hours
3. customAfter completion of the reaction
4. customthe solvent was removed by evaporation in vacuo
5. customthe residue was purified by column chromatography on silica gel (eluent:hexane ethyl acetate/triethylamine=75/25/5)

ORD record

ord-03d686ee575449dfbd9123bf3c381bf5

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07626034B2