Sodium borohydride → HCID 15085907, compound

Participants

Reaction Steps

To a solution of 9.1 g of 17-(cyclopropylimino)-4,4-difluoro-3β-(2-tetrahydropyranyloxy)androst-5-ene in 200 ml of dry ethanol is added 2 g of sodium borohydride. The reaction mixture is stirred at room temperature for 3 hours and then 100 ml of solvent is removed from the mixture under reduced pressure. The reaction mixture is then quenched with dilute acetic acid, diluted with 600 ml of water, and the pH is adjusted to 14 by the addition of sodium hydroxide. The aqueous mixture is extracted 3 times with 600 ml potions of ethyl acetate and the combined organic extracts are dried over magnesium sulfate. Removal of the solvent under reduced pressure gives the desired 17β-(cyclopropylamino)-4,4-difluoro-3β-(2-tetrahydropyranyloxy)androst-5-ene as a white solid. This material is treated with a catalytic amount of hydrochloric acid in dioxane to remove the tetrahydropyranyl protecting group. This compound has the following structural formula: ##STR4##

Provenance & Evidence