| 主权项 |
1. A method for stereoselectively making an aminocyclohexyl ether of the following formula (79), formula (80) or formula (81): wherein R3, R4 and R5 are independently bromine, chlorine, fluorine, carboxy, hydrogen, hydroxy, hydroxymethyl, methanesulfonamido, nitro, cyano, sulfamyl, trifluoromethyl, —CHF2, —SO2N(R8)R9, C2-C7alkanoyloxy, C1-C6alkoxy, C7-C12aralkoxy, C2-C7alkoxycarbonyl, C1-C6thioalkyl, aryl or N(R6)R7 where R6, R7, R8, and R9, are each independently hydrogen, acetyl, methanesulfonyl or C1-C6alkyl; or R3, R4 and R5 are independently hydrogen, hydroxy or C1-C6alkoxy; with the proviso that R3, R4 and R5 cannot all be hydrogen at the same time, which method comprises:(a) reacting a compound of formula (75): where R3, R4 and R5 are as defined above, with a compound of formula (82), a compound of formula (83) or a compound of formula (84): wherein each Lg is independently a leaving group and each R11 is C1-C6alkyl, under suitable conditions to form a compound of formula (85), a compound of formula (86) or a compound of formula (87), respectively: or reacting a compound of formula (75) with a compound of formula (88), a compound of formula (89) or a compound of formula (90): wherein each Lg is independently a leaving group and each R12 is C2-C4acyl or C7-C12aralkyl, under suitable conditions to form a compound of formula (91), a compound of formula (92) or a compound of formula (93), respectively: or reacting a compound of formula (75) with a compound of formula (94), a compound of formula (95) or a compound of formula (96): wherein each R13 is C2-C4acyl or C7-C12aralkyl, under suitable conditions to form a compound of formula (97), a compound of formula (98) or a compound of formula (99), respectively;and(b) reducing the compound of formula (85), the compound of formula (91) or the compound of formula (97) formed in step (a) under suitable conditions to form a compound of formula (79) as set forth above; or
reducing the compound of formula (86), the compound of formula (92) or the compound of formula (98) formed in step (a) under suitable conditions to form a compound of formula (80) as set forth above; or reducing the compound of formula (87), the compound of formula (93) or the compound of formula (99) formed in step (a) under suitable conditions to form a compound of formula (81) as set forth above. |
