Patent ID: 6506908
Filing Date: 2003-01-14
Classification: C07C,C07D

Abstract:
A process for preparing a hydroxymethylcyclopentanone compound of Formula (XII): which comprises(Z4) reacting a mixture comprising a trans-bicyclo[3.1.0]hexane compound of Formula (X): and a nucleophilic agent in solvent at a temperature in a range of from about 20 to about 200Â° C. to open the fused cyclopropyl ring of Compound X by addition of the nucleophile; and(Z5) contacting the reaction mixture of step Z4 with a base to form Compound XII; whereinR1 is phenyl, substituted phenyl, heterocycle, or substituted heterocycle, wherein each of the substituents on substituted phenyl or substituted heterocycle is independently selected from: (a) halo, (b) trifluoromethyl, (c) hydroxy, (d) C1-C3 alkyl, (e) C1-C3 alkoxy, (f) â€”CO2Ra, (g) â€”NRaRb, and (h) â€”CONRaRb; R2 is C1-C4 alkyl, C1-C4 haloalkyl, or C2-C6 alkoxyalkyl; each Ra is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C8 alkoxyalkyl, C5-C6 cycloalkyl, benzyl, phenyl, substituted C5-C6 cycloalkyl, substituted benzyl or substituted phenyl, wherein each of the substituents on substituted C5-C6 cycloalkyl, substituted benzyl or substituted phenyl is independently selected from halo, nitro, C1-C3 alkyl, C1-C3 alkoxy and trifluoromethyl; and each Rb is independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C8 alkoxyalkyl, benzyl, phenyl, â€”C1-C6 alkyl-C3-C6 cycloalkyl, substituted benzyl, substituted phenyl, or substituted â€”C1-C6 alkyl-C3-C6 cycloalkyl, wherein each of the substituents on substituted benzyl, substituted phenyl, or substituted â€”C1-C6 alkylâ€”C3-C6 cycloalkyl is independently selected from halo, nitro, C1-C3 alkyl, C1-C3 alkoxy and trifluoromethyl.