Hydrochloric Acid → HCID 20145926, compound

Participants

Reaction Steps

24 ml of a 1 M diborane solution in tetrahydrofuran are added drop-wise over 2 hours at a temperature of -10° C. to a solution of 2.02 g (6 mMol) of 5-allyloxy-2'-methoxy-2,9,9-trimethyl-6,7-benzomorphan hydrochloride (c.f. example 8f) in 25 ml of tetrahydrofuran. After stirring for 4 hours at room-temperature 16 ml of a 1 N sodium hydroxide solution and 2 ml 30% hydrogen peroxide are carefully added drop-wise. After reaction for 1 hour at room-temperature, 30 ml 1 N hydrochloric acid are added and the mixture is boiled for a further 1 hour under reflux. The tetrahydrofuran is distilled off under reduced pressure, the acid aqueous phase rendered alkali with 25% ammonia and extracted 3 times with 25 ml chloroform. The combined chloroformic phases are dried over magnesium sulphate and concentrated under reduced pressure. After conversion of the residue into the hydrochloric and crystallition from methanol/ether acetate 1.15 g of the title compound are obtained, m.p.: 187°-193° C.

Provenance & Evidence