Methanol → HCID 68415473, compound

Participants

Reaction Conditions

Reaction Steps

Ru(OAc)2((S)-dm-segphos) (0.138 g, 0.147 mmol), tert-butyl 2-benzyloxy-3-oxo-4-phenylbutanoate (5.00 g, 14.7 mmol), ammonium acetate (1.13 g, 14.7 mmol), methanol (25 mL) and tetrahydrofuran (25 mL) were placed in a 200 mL stainless steel autoclave, and the mixture was stirred at 90° C. under a hydrogen pressure of 3 MPa for 13 hours. After completion of the reaction, the solvent was removed by evaporation to give tert-butyl 3-amino-2-benzyloxy-4-phenylbutanoate acetate as a crude material (6.10 g). The ratio of anti and syn diastereoisomer (86:14) was determined by HPLC analysis using a CHIRALPAK AD-RH column (available from DAICEL CHEMICAL INDUSTRIES, LTD). The enantiomeric excess of the crude product was determined to be 98.6% ee (anti diastereoisomer) and 95.1% ee (syn diastereoisomer) by HPLC analysis using a CHIRALCEL OD-H column after conversion into tert-butyl 3-(4-nitrobenzoylamino)-2-benzyloxy-4-phenylbutanoate.

Provenance & Evidence