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The two phases were separated, and the organic phase was washed with brine before being purified by Combi-Flash with a gradient of ethyl acetate from 0:1 to 3:7 to provide the intermediate, phenyl (3-chloro-4-fluorophenyl)carbamate 49 as a white solid (206 mg, 92%); calculated for C13H9ClFNO2, 265.0; observed (M + H) + 266.2. To the intermediate 49 (40 mg, 0.15 mmol, 1.0 eq) in DCM (2 mL), octahydro-4(1H)-quinolinone (23 mg, 0.15 mmol, 1.0 eq) and excess triethylamine was added. Upon completion, the reaction was diluted with EtOAc and washed with 2N HCl twice, saturated NaHCO3, and brine. Purification with Combi-Flash afforded two isomers (32.9 mg and 9 mg respectively) as off-white solids after silica gel separation with a gradient of ethyl acetate: hexanes from 0:1 to 3:7, of which the first peak was the desired cis-N-(3-chloro-4-fluorophenyl)-4-oxooctahydroquinoline-1(2H)-carboxamide (58, 68%). 1H NMR (600 MHz, CDCl3): \u03b4 (ppm) 7.53 (dd, J1 = 6.4 Hz, J2 = 2.6 Hz, H-2\u201ca), 7.19 (ddd, J1 = 8.8 Hz, J2 = 4.0 Hz, J3 = 2.8 Hz, H-6\u201da), 7.06 (t, J1 = 8.7 Hz, H-5\u201ca), 4.4 (m, H-10a), 4.08 (ddd, J1 = 13.2 Hz, J2 = 6.6 Hz, J3 = 5.0 Hz, H-2b), 3.58 (ddd, J1 = 13.1 Hz, 9.8 Hz, 4.5 Hz, H-2a), 2.82 (bs, H-5), 2.58 (ddd, J1 = 15.7 Hz, J2 = 9.6 Hz, J3 = 6.3 Hz, H-3b), 2.48 (ddd, J1 = 15.7 Hz, J2 = 4.7 Hz, J3 = 4.7 Hz, H-3a), 2.38 (dq, J1 = 10.1 Hz, J2 = 2.2 Hz, H-6b), 1.85 (m, H-9b), 1.82 (m, H-8b), 1.53 (m, H-7b), 1.38 (m, H-9a), 1.35 (m, H-8a), 1.30 (m, H-7a), 1.30 (m, H-6a); 13C NMR (151 MHz): \u03b4 (ppm) 208.11 (C-4), 154.6 (C-1'), 153.57 (d, JC-F = 245.4 Hz, C-4\u201d), 135.51 (d, JC-F = 3.3 Hz, C-1\u201c), 122.74 (C-2\u201d), 121.13 (d, JC-F = 18.7 Hz, C-3\u201c), 120.15 (d, JC-F = 6.6 Hz, C-6\u201d), 116.62 (d, JC-F = 21.9 Hz, C-5\u201c), 55.68 (C-10), 49.09 (C-5), 39.99 (C-3), 39.86 (C-2), 29.65 (C-9), 25.34 (C-8), 24.67 (C-6), 21.33 (C-7); HRMS, Calculated for C16H18ClFN2NaO2, 347.0933; observed (M+Na)+ 347.0925. 58 (77.3 mg) was further purified on CHIRALPAK IF column eluted with acetonitrile-ethanol (7:3) to provide two chiral factions, 32.1 mg (42%) and 28.7 mg (37%) respectively both with ee > 99%. 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