350029-02-6Relevant articles and documents
Synthesis and transformations of 2-(phenylhydroxymethyl)cyclohexylamines
Csomós, Péter,Bernáth, Gábor,Sohár, Pál,Csámpai, Antal,De Kimpe, Norbert,Fül?p, Ferenc
, p. 3175 - 3183 (2001)
Diastereomeric 2-(phenylhydroxymethyl)cyclohexylamines were synthesised by reduction of 2-benzoylcyclohexylamines. (1S*,2R*)-2-Benzoylcyclohexylamine can be reduced diastereoselectively to the corresponding γ-amino alcohol with sodium borohydride; for the trans counterpart (1R*,2R*)-2-benzoylcyclohexylamine, lithium aluminium hydride was found to be a selective reducing agent. In both cases, high syn selectivities were observed. The amino alcohols were transformed to the corresponding cyclohexane-fused tetrahydro-1,3-oxazin-2-ones and -2-thiones. The γ-amino alcohols reacted with arylimidates to afford 4,5-dihydro-6H-1,3-oxazines. Their cyclization with phenyl isothiocyanate yielded 2-phenyliminotetrahydro-1,3-oxazines.