Synthesis and transformations of 2-(phenylhydroxymethyl)cyclohexylamines

Diastereomeric 2-(phenylhydroxymethyl)cyclohexylamines were synthesised by reduction of 2-benzoylcyclohexylamines. (1S*,2R*)-2-Benzoylcyclohexylamine can be reduced diastereoselectively to the corresponding gamma -amino alcoh ol with sodium borohydride; for the trans counterpart (1R*,2R*)-2-benzoylcy clohexylamine, lithium aluminium hydride was found to be a selective reduci ng agent. In both cases, high syn selectivities were observed. The amino al cohols were transformed to the corresponding cyclohexane-fused tetrahydro-1 ,3-oxazin-2-ones and -2-thiones. The gamma -amino alcohols reacted with ary limidates to afford 4,5-dihydro-6H-1,3-oxazines. Their cyclization with phe nyl isothiocyanate yielded 2-phenyliminotetrahydro-1,3-oxazines. (C) 2001 E lsevier Science Ltd. All rights reserved.