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0 °C

To a stirred solution of 4-[(4-bromo-phenoxy)-difluoro-methyl]-cyclohexanone (1050 mg, 3.290 mmoles) in ethanol (16.4 mL, 0.2M) was added NaBH4 (249 mg, 6.58 mmoles) 0° C. The solution was stirred at 0° C. for 20 minutes and then warmed to room temperature for 20 minutes. The reaction was quenched with 1 N HCl to a pH of ˜7, and extracted three times with ethyl acetate. The organics where combined, dried over magnesium sulfate, filtered and concentrated. Cis/trans isomers were then separated by chiral purification. Isolated 260 mg of trans isomer (24%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.39 (s, 2 H) 1.51-1.65 (m, 2 H) 1.83-1.96 (m, 2 H) 2.01-2.21 (m, 2 H) 2.38-2.47 (m, 1 H) 7.03-7.14 (m, 2 H) 7.41-7.58 (m, 2 H)

1. temperaturewarmed to room temperature for 20 minutes
2. customThe reaction was quenched with 1 N HCl to a pH of ˜7
3. extractionextracted three times with ethyl acetate
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customCis/trans isomers were then separated by chiral purification
8. customIsolated 260 mg of trans isomer (24%)