Acetic Acid → (2R,3R)-3-hydroxy-8-methyl-2-(4-methylphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of D-tert-leucine (289 mg), sodium borohydride (76 mg) and tetrahydrofuran (15 ml) is refluxed under nitrogen atmosphere for three hours. The mixture is cooled to -10° C., and thereto is added a solution of 8-methyl-2-(4-methyl-phenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione (297 mg) in tetrahydrofuran (3 ml). The mixture is stirred at -10° C. for 17 hours, and thereto is added acetic acid (600 mg). The mixture is evaporated under reduced pressure to remove the solvent. To the residue is added water (10 ml), and the precipitated crystal is collected by filtration, washed with water, and dried to give (2R,3R)-3-hydroxy-8-methyl-2-(4-methylphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (280 mg).

Provenance & Evidence