Patent ID: 7754897

Claim:
A method of making a compound of formula (I): or a pharmaceutically acceptable salt, ester, amide, clathrate with a cyclodextrin or solvate in a solution phase thereof as a single stereoisomer or as a mixture thereof; wherein: R 3 , R 4 and R 5 are independently bromine, chlorine, fluorine, carboxy, hydrogen, hydroxy, hydroxymethyl, methanesulfonamido, nitro, cyano, sulfamyl, trifluoromethyl, —CHF 2 , —SO 2 N(R 8 )R 9 , —OCF 3 , C 2 -C 7 alkanoyloxy, C 1 - C 6 alkyl, C 1 -C 6 alkoxy, C 7 -C 12 aralkoxy, C 2 -C 7 alkoxycarbonyl, C 1 -C 6 thioalkyl, aryl or —N(R 6 )R 7 ; and R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, acetyl, methanesulfonyl or C 1 -C 6 alkyl; which method comprises: a) reacting a compound of formula (4): wherein each R 2a is O or H 2 where at least one R 2a in the compound of formula (4) is O, and R is H, C 2 -C 5 acyl or an oxygen-protecting group, with a compound of formula (5): wherein R 3 , R 4 and R 5 are as defined above and Q is a leaving group, to form a compound of formula (6): wherein each R 2a is O or H 2 where at least one R 2a is O, R is H, C 2 -C 5 acyl or an oxygen-protecting group and R 3 , R 4 and R 5 are as defined above, under suitable conditions such that upon reaction of the compound of formula (4) with the compound of formula (5), the trans relative configuration of the hydroxyl group on the carbon at the 1-position of the compound of formula (4) is retained in the carbon at the 1-position of the compound of formula (6); b) reducing the compound of formula (6) under suitable conditions to form a compound of formula (I).