Sodium Hydroxide → (2R)-(3-[3-[2-(3-chlorophenyl)-2-hydroxyethylamino]cyclohexyl]phenoxy) acetic acid

Participants

Reaction Steps

To a solution of the trans-H compound, (1R)-1-(3-chlorophenyl)-2-[3-(3-ethoxycarbonylmethoxyphenyl)cyclohexylamino]ethanol (hydrochloride), obtained in Example 11 (220 mg) in ethanol (10 ml) there was added 1 N sodium hydroxide solution (2.5 ml), and the mixture was stirred at room temperature for 2 hours. After concentrating the reaction solution under reduced pressure, water (2 ml) was added, and after adding 1 N aqueous solution of hydrochloric acid (2.03 ml) while stirring and cooling on ice, the deposited crystals were filtered off and dried to give 153 mg of (2R)-(3-[3-[2-(3-chlorophenyl)-2-hydroxyethylamino]cyclohexyl]phenoxy) acetic acid (trans-H) as a white crystalline powder (81% yield).

Provenance & Evidence