3-[2-hydroxy-4-(substituted) phenyl-4(or-5)- substituted...

Details 3-[2-hydroxy-4-(substituted) phenyl-4(or-5)- substituted... 3-[2-hydroxy-4-(substituted) phenyl-4(or-5)- substituted...

C - Chemistry, Metallurgy

07

C

260/295, 260/489

C07C 49/753 (2006.01)

Patent

CA 1183538

ABSTRACT OF THE DISCLOSURE Novel 3-[2-hydroxy-4-(substituted)phenyl-4(or -5)-substituted cyclo- alkanones of the formula Image (II) wherein R1 is hydrogen, alkanoyl, or hydroxy-protecting group; S is 1 or 2; W is hydrogen, pyridyl or Image W1 wherein W1 is H, Cl or F; Z is alkylene, -(alkl)m-0-(alk2)n wherein (alkl) and (alk2) are alkylene, m and n are 0 or 1, Y1 is -CH(R2")CH(R2)- or -CH(R3)CH2- wherein R2" is H or CH3, R2 and R3 are hydroxy alkyl, are prepared by (A) hydrating a compound of the formula or a ketal thereof Image (II-B) wherein Y" is -CH(R2")CII(R2°)- or -CH(R3°)CH2- wherein R2° and R3° are alkenyl, or (B) reducing oxo-alkyl R2°° or R3°° in a compound of tho formula or a kotal thereof Image wherein Y? is -CH(R2")CH(R2°°)- or -CH(R3°°)CH2- wherein R2°° and R3°° are oxo-alkyl, to hydroxy-alkyl, or (C) subjecting the compound of formula (II-C), or a ketal thereof to the Gripnard reaction. The compounds of formula (II)are useful as analgesic agents and anti-emetic agents, and also as intermediates for preparing the corresponding cycloalkanols.

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