Preparation of N-substituted-hydroxycycloalkylamine derivatives

• Main Authors: KIM SEONG JIN, YANG KYOUNG YOUL, KIM KEON IL
• Format: Patent
• Language: English
• Published: 20.05.2003
• Edition: 7
• Subjects: APPARATUS THEREFOR; CHEMISTRY; CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION ORPROCESSING OF GOODS; GENERAL METHODS OF ORGANIC CHEMISTRY; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS; TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINSTCLIMATE CHANGE

A process for the preparation of N-substituted-hydroxycycloalkylamine derivatives, that are useful intermediates for the synthesis of various organic chemicals including pharmaceutical and agrochemical compounds, represented by formula (1), by reacting a 1,2-dihydroxalkyl alcohol, represented by the following formula (2), with a thionyl halide to produce an intermediate 1,2-cyclosulfinylalkyl halide represented by the following formula (3); and then cyclizing that intermediate with an amine compounds represented by the following formula (4).In the above structural formuli, * represents an asymmetric carbon atom; R1 is hydrogen or an amino-protecting group; m is an integer of 1-3; and X is halogen. The reactant compounds as well as the compounds made according to this invention have the following substitution pattern:n=1, R2=OH, R3=H and m=1; n=1, R2=H, R3=CH2OH and m=2;n=2, R2=OH, R3=H; and m=2; and n=2, R2=H, R3=CH2OH and m=3.