131227-41-3Relevant academic research and scientific papers
Behaviour of the gem-cyano-ethoxycarbonyl cyclohexane, thiopyran and pyran derivatives with sodium borohydride and lithium aluminium hydride
Gonzalez, F. Santoyo,Garcia, J. Isac,Mendoza, P. Garcia,Diaz, R. Robles,Martinez, J. J. Gimenez,et al.
, p. 5673 - 5684 (1990)
Treatment of the gem-cyano ethoxycarbonyl compounds 1a-c with NaBH4 in 2-propanol or PEG-400 produced reduction of the ethoxycarbonyl group and simultaneous reductive deacetoxylation.Similar treatment of 7 with NaBH4-CoCl2 produced selective reduction of the cyano group to aminomethyl group and rearrangement O->N of an acetyl group to aminomethyl group.Treatment of 1a-c and 7 with LiAlH4 gave, after acetylation, the gem-aminomethyl-hydroxymethyl compounds 6a-c and 11 respectively.Compounds 4a-b, 5a-b and 6a-b show a prefered conformation with both acetoxy groups in an equatorial disposition.However compounds 4c, 5c and 6c prefer the conformation with both acetoxy groups in an axial disposition.
