6α-Acet­oxy-4,5α-ep­oxy-3-meth­oxy-17-meth­ylmorphin-7-ene

Crystals of the title compound, which is also commonly known as 6-O-acetyl­codeine, C₂₀H₂₃NO₄, were obtained by acetyl­ation of codeine and subsequent crystallization of the product from eth­yl acetate. The atoms of the benzene ring are nearly coplanar, whereas the five-memberedring is distorted. The ethanamine ring has a typical chair form conformation, while the cyclohexene ring is in a twisted boat form.

A (1R,2R,5R)-(+)-2α-hydroxy­pinan-3-one ketimine

The title compound {systematic name: (1R,2R,5R)-(+)-2-hydr­oxy-2,6,6-trimethyl-3-[(3-pyrid­yl)methyl­imino]­bicyclo[3.1.1]­heptane}, C₁₆H₂₂N₂O, was obtained by the condensation reaction of (1R,2R,5R)-(+)-2α-hydroxy­pinan-3-one with 3-(amino­meth­yl)pyridine in the presence of boron trifluoride. The compound was obtained as an enantiomerically pure isomer, and has the 1R,2R,5R configuration. In the crystal structure, mol­ecules are linked together by inter­molecular O—H...N hydrogen bonds between the hydr­oxy group of the pinanone group and the N atom of the pyridine ring, forming mol­ecular chains.