The preparation of n-substituted-hydroxycycloalkylamine...

C - Chemistry – Metallurgy – 07 – D

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C07D 207/12 (2006.01) C07D 207/08 (2006.01) C07D 211/18 (2006.01) C07D 211/22 (2006.01) C07D 211/42 (2006.01) C07D 327/10 (2006.01)

Patent

CA 2343837

The present invention relates to the preparation of N-substituted- hydroxycycloalkylamine derivatives and more particularly, to the method for synthesis of N-substituted-hydroxycycloalkylamine derivatives represented in formula (1), regioselectively in high yield via 1,2-cyclosulfinyl halide as an intermediate from the 1,2-dihydroxyalkyl alcohol as a starting material. In said formula, * represents an asymmetric carbon; R1 is hydrogen, linear alkyl, branched alkyl, or cycloalkyl containing 110 carbon atoms or typical amino- protecting groups such as aromatic hydrocarbons; n is 1 or 2, with the proviso that if n=1 then R2=OH and R3=H or R2=H and R3=CH2OH, if n=2 then R2=OH and R3=H or R2=H and R3=CH2OH.

Préparation de dérivés d'hydroxycycloalkylamine à substitution N et plus particulièrement procédé de synthèse, stéréosélective et à haut rendement, de dérivés d'hydroxycycloalkylamine à substitution N représentés par la formule (1), à l'aide d'halogénure de 1,2-cyclosulfinyle comme intermédiaire provenant d'alcool de 1,2-dihydroxyalkyle en tant que matière de départ. Dans ladite formule, * représente un carbone asymétrique; R?1¿ est hydrogène, alkyle linéaire, alkyle ramifié, ou cycloalkyle contenant 1 à 10 atomes de carbone ou des groupes amino-protecteurs typiques tels que des hydrocarbures aromatiques; et n est 1 ou 2 à condition que lorsque n est égal à 1, R¿2? est OH et R¿3? est H ou R¿2? est H et R¿3? est CH¿2?OH, et lorsque n est égal à 2, R¿2? est OH et R¿3? est H ou R¿2? est H et R¿3? est CH¿2?OH.

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