Synthesis of?-amino-?-cyclohexylpropionic acid and CF some of its derivatives

Abstract

1. Rodionov's method for synthesis ofβ-amino acids has been extended to aldehydes of the alicyclic series. 2. A simple method of preparation of hexahydrobenzaldehyde or cyclopentylmaldehyde from cyclohexyl-or cyclopemyl-glycidic ester, respectivelu, is described. 3. Condensation of hexahydrobenzaldehyde with malonic acid leads to formation ofβ-amino-β-cyclohexylpropionic acid, in 50% yield. 4. The yield ofβ-amino acid is raised to 66% when the aldimine is taken for the condensation instead of the free sidehyde. 5. The N-benzoyl, N-acetyl-, and N-carbomethoxy-derivatives ofβ-amino-β-cyclohexylpropionic acid and its amide are described, as well asβ-ureodi-β-cyclohexylpropionic acid and cyclohexyldihydrouracil. 6. The Hoffmannreaction is carried out with the acylated derivative of the aminopropiomanides, and it is shown that the N-benzoyl- and N-carbomethoxy-derivatives give 5-cyclohexylglyoxalidone and its N-benzoyl-or N-carbpmethoxy-derivatives. β-Acetamide-β-cyclohexylpropionamide gives only cyclohexylglyoxalidone when treated with hypobromite. 7. The formation of acylated cyclohexylglyoxalidones confirms the correctness of mechanism propored by Rodionoc and Zvorykina [4] for the Hoffmann reaction ofβ-amino acids.