Patent ID: 8119842

Claim:
A method of producing a compound of formula k1 or k2 wherein: m is 0 or 1; n is from 0 to 3; Ar is: aryl; or heteroaryl, each of which may be optionally substituted with: halo; C 1-6 alkyl; C 1-6 alkoxy; cyano; hydroxy; C 1-6 alkylsulfonyl; or halo-C 1-6 alkyl; Y is —O—; —S(O) p — or —N—R a wherein p is from 0 to 2 and R a is hydrogen or C 1-6 alkyl; and R 1 is: halo; C 1-6 alkyl; C 1-6 alkoxy; or halo-C 1-6 alkyl; the method comprising: reducing a dihydronapthalene amide compound of formula i with hydrogen gas in the presence of a catalyst of formula j1 or j2 Ru(Z) 2 (L) j1; Ru(E)(E′)(L)(D) j2; wherein: D is an optionally chiral diamine; E and E′ are both halo, or E is hydrogen and E′ is BH 4 ; L is a chiral diphosphine ligand; and Z is: halo or R b —CO 2 − (carboxylate) wherein R b is: C 1-6 alkyl; halo-C 1-6 alkyl; C 1-6 alkoxy; aryl optionally substituted with halo; or heteroaryl optionally substituted with halo.