p-Toluenesulfonic acid monohydrate → HCID 23112193, compound

Participants

Reaction Steps

A solution of Intermediate 9 (5.73 g), Intermediate 1 (2.92 g), and para-toluenesulfonic acid monohydrate (163 mg, Wako Pure Chemical Industries) in toluene (50 ml) was refluxed by heating for 1 hour. The reaction mixture was cooled to room temperature, then added with methanol (75 ml) and sodium borohydride (6.48 g), and stirred at room temperature for 1 hour. The reaction mixture was added with water (5 ml), and then the solvent was evaporated under reduced pressure. The residue was added with ethyl acetate (100 ml), and the organic layer was washed twice with water (50 ml), and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (2.2 g of trans-isomer, 1.8 g of cis-isomer).

Provenance & Evidence