Ammonium Chloride → 4-Dimethylamino-4-phenyl-1-(5-triethylsilanyl-pent-4-inyl)cyclohexanol

Participants

Reaction Conditions

Reaction Steps

A 1.7 M solution of tert-butyl lithium (18.4 mL, 31.2 mmol) in pentane was incorporated directly by cannula into a solution of triethyl-(5-iodopent-1-inyl)silane (4.81 g, 15.6 mmol) in anhydrous diethyl ether (150 mL) at −75° C. with argon, wherein the inside temperature was held between −70° C. and −75° C. After stirring for 2 h at −75° C. a solution of 4-(dimethylamino)-4-phenylcyclohexanone (3.39 g, 15.6 mmol, synthesis cf. WO2008009415, ketone unit Ket-10) in anhydrous diethyl ether (150 mL) was slowly added in drops, stirred for a further 30 min at −75° C. and the reaction solution was then heated to room temperature. The reaction mixture was then mixed with saturated ammonium chloride solution (100 mL), the phases were separated, the aqueous phase extracted with diethyl ether (3×50 mL), the combined organic phases washed with sodium chloride solution (50 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product was purified by means of flash chromatography (400 g, 20×7.5 cm) with ethyl acetate/methanol (9:1).

Provenance & Evidence