(−)-4-Hydroxy-N-formylmorphinan-6-one, a versatile intermediate for the synthesis of 3-deoxyopioids

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Abstract
(−)-4-Hydroxy-N-formylmorphinan-6-one (4) was prepared in 70% overall yield from ketone 1, via carbamate 2, and N-formylation of ketone 3. Bromination of 4 afforded either the 6-ketomorphinan 7 or the ketone 8, depending on the reaction conditions applied. Both bromo ketones 7 and 8 could be converted by standard reactions into 4,5-epoxy-N-methylmorphinan-6-one (1). The ketomorphinan 4 emerges from these investigations as a versatile intermediate, well suited for the synthesis of 4-hydroxymorphinans and 3-deoxyopioids.

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