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The reaction that occurs when vapors of 2,2-dimethylpropanal and methanamine are allowed to mix in an infrared gas cell has been examined. The disappearance of starting materials and formation of E-imine product, monitored simultaneously, is best fit by a process involving wall-associated water. The same or closely related processes have been successfully modeled; such processes may also be common to pyridoxal-catalyzed transamination and related reactions in biological systems.

Improved protocols for the preparation of 1-bromodihydrocodeinone (1-bromohydrocodone) and 1-bromo-14-hydroxydihydrocodeinone (1-bromooxycodone) and synthesis of the corresponding 1-chloro and 1-iodo derivatives have been achieved using the corresponding N-halosuccinimides in acidic milieu. The corresponding 1-carboethoxy derivative of 14-hydroxydihydrocodeinone (1-carboethoxyoxycodone) has been prepared by Pd-catalyzed reaction with carbon monoxide in ethanol. The ester was hydrolyzed to the corresponding zwitterionic amino acid.

Beginning with (+)-serine or (-)-serine, as appropriate, convenient, high-yield, enantioselective synthesis of all eight stereoisomeric 2-hydroxymethyl-3,4-dihydroxypyrrolidines (the enantiomeric pairs of iminoribitol, -arabinitol, -xylitol, and -lyxitol) can be effected. The absolute configuration of the starting amino acid defines the set of azasugars produced.