HCID 12515637, compound → HCID 12515638, compound

Participants

Reaction Steps

3.5 Parts by volume of 1.5 M solution of lithium perhydro-9b-boraphenallyhydride in tetrahydrofuran is added to a stirred, cold (-78° C.) solution of 0.65 part of 1-(2,2-diphenylethyl)-3-[1-(2,2-diphenylethyl)-4-hydroxypiperidin-4-yl]-4-piperidinone in 25 parts by volume of tetrahydrofuran under nitrogen atmosphere. The reaction is allowed to run for about 30 minutes and then it is quenched with the addition of 25 parts by volume of 10% ammonium chloride solution. Ethyl ether is added to the reaction mixture and it is allowed to warm to room temperature. After 2 hours the organic layer is separated and then extracted twice with 10% hydrochloric acid. The combined acid extracts are made alkaline with 50% sodium hydroxide and then extracted twice with ethyl ether. The organic fractions are combined, dried, and concentrated to yield yellow gum which crystallizes when triturated with ethyl ether to afford 1-(2,2-diphenylethyl)-3-[1-(2,2-diphenylethyl)-4-hydroxypiperidin-4-yl]-4 -piperidinol. This compound melts at about 174°-175° C. after recrystallization from absolute ethanol, and is represented by the following structural formula ##STR39##

Provenance & Evidence