Hydrochloric Acid → HCID 70623907, compound

Participants

Reaction Steps

A solution of 4.5 g of borane in 300 ml of tetrahydrofuran (THF) is cooled to -5° under a stream of nitrogen, and then a solution of 35 g of N-cyclobutylcarbonyl-3-methoxy-14-hydroxy-6-ketomorphinan in 200 ml of THF is added slowly over a 45 minute period, keeping the reaction temperature below 0° C. The reaction mixture is then refluxed for 3 hours, cooled, and 150 ml of ZN HCl is added slowly, which induces a vigorous evolution of gas. The solution is then evaporated to a volume of 150 ml in vacuo, diluted with 200 ml of water, and the pH adjusted to 9.0 by the careful addition of 14 N ammonium hydroxide. The precipitate is stirred for two hours and filtered to give crude N-cyclobutylmethyl-3-methoxy-6α,14β-di-hydroxymorphinan.

Provenance & Evidence