Sodium Hydroxide → (E)-1-[3-(4-hydroxy-3-methoxyphenyl)-2-propenyl]-4-(4-phenoxyphenyl)piperidine

Participants

Reaction Steps

To an 8 ml tetrahydrofuran solution of 400 mg of the compound (5) synthesized in Reference Example 5 was added under ice cooling 60 mg of lithium aluminum hydride, then the resulting mixture was stirred at room temperature for two hours. A 10% aqueous solution of sodium hydroxide solution was added, then the product was extracted with methylene chloride. The extract was dried, filtered, then concentrated under reduced pressure to obtain a residue which was then purified by silica gel column chromatography (methylene chloride:methanol=20:1) to obtain the above-referenced compound (19) in an amount of 273 mg (yield 72%).

Provenance & Evidence