rac-Diethyl 6-hydroxy-4-[(2-hydroxyethyl)amino]-6-methyl-2-phenylcyclohex-3-ene-1,3-dicarboxylate

Abstract

The title compound, C21H29NO6, is chiral with three stereogenic centres. The crystal is a racemate and consists of enanti­omeric pairs with the relative configuration rac-(2R*,3S*,4R*). The ethyl fragment of the eth­oxy­carbonyl group at position 1 is disordered in a 0.60:0.40 ratio. The crystal packing displays inter­molecular O—H⋯O hydrogen bonding. An intra­molecular N—H⋯O hydrogen bond also occurs.

Syntheses and some features of five new cyclohexane-1,3-dicarboxylates with multiple stereogenic centers

“…The methods of further modification of the thus prepared cyclohexanones with mono-or polyfunctional nucleophiles are also well studied [20][21][22][23][24][25][26][27][28]. For instance, it was found that reactions of hydroxylamine [9], hydrazine [23,24], ethylenediamine [27], ethanolamine [8,26,27], ethylene glycol [4], substituted aromatic amines [20,21,25], tosylhydrazide [22] and benzidine [28] with diethyl-4-hydroxy-4-methyl-6-oxo-2-phenylcyclohexane-1,3-dicarboxylate give isoxazole, imidazole and 1,3-dioxolane rings, Schiff base condensation products, etc. Moreover, in some cases the cyclization processes depend on temperature, i.e.…”