Patent ID: 8163938

Claim:
A method of stereoselectively making an aminocyclohexyl ether comprising: reacting a compound of formula (55), or a compound of formula (74), with a compound of formula (56), to form a compound of formula (57), or a compound of formula (75), respectively, wherein R 1 and R 2 , when taken together with the nitrogen atom to which they are directly attached in formula (57) or (75), form a ring denoted by formula (II): wherein the method further comprises making the compound of formula (74) or formula (55) by activating a compound of formula (73), or a compound of formula (94), with a hydroxy activating reagent to form the compound of formula (74) or the compound of formula (55), respectively; wherein the method further comprises making a compound of formula (73) by hydrogenating and hydrogenolyzing a compound of formula (72), to form the compound of formula (73); wherein the method further comprises making a compound of formula (72) by alkylating a compound of formula (51), with a compound of formula (54), to form the compound of formula (72); wherein X is a halide; wherein O-J is a leaving group; wherein R 3 , R 4 and R 5 are independently selected from hydrogen, hydroxy, and C 1 -C 6 alkoxy, with the proviso that R 3 , R 4 and R 5 cannot all be hydrogen; and wherein O-Q is a leaving group that reacts with —OH in the compound of formula (51) to form the compound of formula (72), such that the stereochemical configuration of the compound of formula (51) is retained in the compound of formula (72).