Ammonium Acetate → Methyl 3-amino-3-(2-thienyl)propanoate

Temperature

80 °C

Ru(OCOCH3)2((S)-segphos)(45.0 mg, 0.543 mmol), methyl 2-(2-thenoyl)acetate (1.00 g, 5.428 mmol), ammonium acetate (0.418 g, 5.428 mmol) and methanol (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 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 silica gel chromatography (eluent hexane ethyl acetate/triethylamine=50/50/5) to give methyl (+)-3-amino-3-thiophen-2-yl-propionate (270 mg) as a colorless oil in 26.8% yield. The resulting methyl (+)-3-amino-3-thiophen-2-yl-propionate was converted into methyl 3-(4-nitrobenzoylamino)-3-thiophen-2-yl-propionate, and the enantiomeric excess of the product was found to be 95.7% ee by HPLC analysis using a SUMICHIRAL OA-4100 column (available from SUMIKA CHEMICAL ANALYSIS SERVICE LTD.).

1. temperatureThe reaction mixture was cooled down to room temperature
2. stirringfurther 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 silica gel chromatography (eluent hexane ethyl acetate/triethylamine=50/50/5)

ORD record

ord-35c49c35402843108b863848f439fb39

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07626034B2