2 2 4 91 dd 1h j 1 12 4 j 2 2 3 4 59 dd 1h j 1 12 4 j 2 2 1 4 13 4 38 br 1h selected minor isomer peaks u03b49 13 dd 1h j 1 8 1 j 2 1 7 7 91 dt 1h j 1 7 9 j 2 1 7 4 94 dd 1h j 1 9 8 j 2 2 6 4 76 dd 1h j 1 12 8 j 2 2 8 to a solution of oxime 3 2 51 kg 14 02 mol in methanol 49 l at 0 u00b0 c was charged 48 aqueous hbr 1 94 l maintaining the temperature below 5 u00b0 c 10 palladium on carbon 2 kg 62 water wet was charged and the mixture was hydrogenated in a five gallon stirred autoclave at 5 u00b0 c 40 psig for 12 hr cis trans 20 1 89 assay yield of cis isomer the mixture was filtered through solka floc and washed with methanol to give a solution of the hbr salt 4 in methanol 85 l the batch was eluted through dowex 1 u00d7 2 19 l on the base cycle using methanol 72 l the solution of free base amine 5 was solvent switched to ethanol 44 l kf u2266 550 ug ml under reduced pressure the free base amine in ethanol was heated to 70 u00b0 c and s mandelic acid 2 1 kg 14 mol in ethanol 3 l was added the mixture was cooled to 15 u00b0 c over 3 hr the salt 6 was isolated by filtration and washed with ethanol 3 5 l the batch was dried under vacuum at 20 u00b0 c to give.