Diethyl Ether → HCID 22612281, compound

Participants

Reaction Conditions

Reaction Steps

To a 4-({[2-(3-Chloro-phenoxy)-pyridine-3-carbonyl]-amino}-methyl)-cyclohexanecarboxylic acid ethyl ester (0.220 grams, 0.53 mmole) in tetrahydrofuran (5 ml) at −78° C. 1.4 M methyl lithium in diethyl ether (1.13 ml, 1.58 mmole) was added dropwise to keep the temperature below −60° C. and stirred at −78° C. for 2 hours and allowed to warm to room temperature. The mixture was quenched with sat'd NH4Cl and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over Na2SO4, filtered and concentrated to a product which was purified by chromatography on silica eluting with 2/3 ethyl acetate/hexane to give an off-white oil. (0.040 g); 1H NMR (400 mhz, CDCl3) d 0.84-1.70 (m, 12H), 1.83-1.87 (m, 4H), 3.30-3.37 (m, 2H), 7.04-7.07 (m, 1H), 7.11-7.19 (m, 2H), 7.24-7.27 (m, 1H), 7.35-7.39 (m, 1H), 7.79 (bs, 1H),8.19-8.21 (m, 1H), 8.60-8.62 (m, 1H).

Provenance & Evidence