Methyl 5-methyl-3-oxohexanoate → HCID 86036461, compound

Participants

Reaction Conditions

Reaction Steps

Ru(OAc)2((R)-dm-binap) (0.201 g, 0.211 mmol), methyl 5-methyl-3-oxohexanoate (10.00 g, 63.2 mmol), ammonium acetate (5.02 g, 63.2 mmol) and methanol (50 mL) were placed in a 100 mL stainless steel autoclave under nitrogen atmosphere, and then the mixture was stirred under a hydrogen pressure of 3 MPa at 80° C. for 24 hours. After completion of the reaction, the solvent was removed by evaporation to give methyl (−)-3-amino-5-methylhexanoate acetate as a crude material (12.70 g). The crude product was treated with 7N ammonia/methanol and analyzed by GLC using a capillary column TC-5HT, indicating that the yield of methyl 3-amino-5-methylhexanoate was 74.4%. The enantiomeric excess of methyl (−)-3-amino-5-methylhexanoate in the crude product was determined to be 97.7% ee by HPLC analysis using a SUMICHIRAL OA-4100R column after conversion into methyl 3-(4-nitrobenzoylamino)-5-methylhexanoate.

Provenance & Evidence