Patent ID: 7786329

Claim:
A process for preparing a compound of Formula XI: wherein: R 1 is hydrogen, methylthio, methylsulfoxy, methylsulfonyl, fluoromethylthio, fluoromethylsulfoxy, fluoromethylsulfonyl, nitro, fluoro, bromo, chloro, acetyl, benzyl, phenyl, halo substituted phenyl, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 aralkyl, C 2-6 aralkenyl, or C 2-6 heterocyclic group; and R 7 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 dihaloalkyl, C 1 trihaloalkyl, C 3-8 cycloalkyl, C 3-8 cyclohaloalkyl, C 3-8 cyclodihaloalkyl, C 3-8 cyclotrihaloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 aralkyl, C 2-6 aralkenyl, C 2-6 heterocyclic benzyl, phenyl or phenyl alkyl where the phenyl ring may be substituted by one or two halogens, C 1-6 alkyl or C 1-6 alkoxy comprising: a) reacting a compound of Formula VI: wherein: R 1 is as defined above; R 5 is hydrogen, C 1-6 alkyl, C 3-8 cycloalkyl, benzyl, phenyl or C 1-6 phenylalkyl with an oxazolidine forming reagent to form a compound of Formula XIV: wherein: R 1 and R 5 are as defined above; R 2 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 aralkyl, C 2-6 aralkenyl, aryl, or C 2-6 heterocyclic group; R 3 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 aralkyl, C 2-6 aralkenyl, aryl or C 2-6 heterocyclic group; b) reducing in situ the compound of Formula XIV with a reducing agent in an alcoholic solvent to form a compound of Formula VIII: wherein: R 1 , R 2 and R 3 are as defined above; c) reacting the compound of Formula VIII in situ with a third N-acylating agent to form an oxazolidine protected aminodiol compound of Formula XII: wherein: R 1 , R 2 , R 3 and R 7 are as defined above; d) fluorinating the compound of Formula V with a fluorinating agent in the presence of an organic solvent to obtain a compound of Formula XIII: wherein: R 1 , R 2 , R 3 and R 7 are as defined above; and e) selectively hydrolyzing the compound of Formula XIII with an acid or base catalyst to form a compound of Formula XI.