Tetrahydrofuran → HCID 86752621, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 162 mL of 0.5M potassium bistrimethylsilylamide in toluene and 600 mL of anhydrous tetrahydrofuran cooled to -78° C. under nitrogen atmosphere was added dropwise a solution of 7.5 g of (±)-methyl 2-(2-methoxycarbonylethyl(1-propyl)amino)butyrate in 50 mL of dry (tetrahydrofuran over 20 min, keeping the internal temperature under -70° C. The mixture was allowed to warm to -20° C. for 2 h, then quenched with 100 mL of saturated aqueous sodium bicarbonate and extracted into 3×200 mL portions of ethyl acetate. The combined extracts were dried over MgSO4 and concentrated under reduced pressure. There was obtained 6.6 g of predominantly (±)-trans-5-carbomethoxy-2-methyl-4-oxo-1-propyl piperidine as an oil: TLC (EtOAc); 1H NMR (400 MHz, CDCl3) 3.76 (s, 3H), 3.2 (m, 1H), 2.9 (m, 1H), 2.62-2.0 (complex m, 6H), 1.5 (m, 2H), 1.25 (d, 3H), 0.5 (dd, 3H).

Provenance & Evidence