Ethyl Acetate → HCID 68811023, compound

Participants

Reaction Steps

(4-Fluoro-phenyl)-piperidin-4-yl-methanone (0.15 g, 0.73 mmol) is added to a solution of ((R)-2-Bromo-1-pyridin-3-ylmethyl-ethyl)-carbamic acid tert-butyl ester (0.21 g, 0.66 mmol) and 1,8 diazabicyclo[5.4.0]undec-7-ene (0.12 ml, 0.79 mmol) in dimethylformamide (3 ml). The reaction mixture is stirred at ambient temperature for 24 hours prior to partioning between ethylacetate and water. The ethylacetate is dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (97:3 dichloromethane: methanol elution) to afford {(R)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-1-pyridin-3-ylmethyl-ethyl}-carbamic acid tert-butyl ester. 1H NMR (400 MHz, CDCl3) δ 1.36 (s, 9H), 1.68-1.85 (br m, 4H), 2.00-2.38 (br m, 4H), 2.78-2.91 (m, 4H), 3.05-3.19 (m 1H), 3.81-3.93 (m 1H) 7.05 (t J 8.8 2H), 7.12-7.18 (m 1H), 7.48 (d J 7.9 1H), 7.85-7.93 (dd J 8.8 5.4 2H), 8.36 (d J 1.5 1H), 8.40 (dd J 4.9 1.5 1H).

Provenance & Evidence