Hydrochloric Acid → HCID 59252699, compound

Participants

Reaction Steps

To a 0° C. solution of 0.86 g (2.2 mmol) ethyl 4-[acetyl(3-fluorophenyl)amino]-1-benzylpiperidine-4-carboxylate in 1 mL THF was added 3.2 mL (6.5 mmol, 2M solution in heptane, THF, ethylbenzene) lithium diisopropylamide solution and the reaction mixture was allowed to slowly warm to rt and stirred for an additional 14 hr. To this mixture was added 50 mL water and 50 mL EtOAc and the pH was adjusted to pH=6 with 1N HCl (approx 11 mL). The aqueous layer was extracted 3×100 mL EtOAc and the combined extracts washed with 100 mL brine, dried over MgSO4, filtered, and concentrated to give 8-benzyl-1-(3-fluorophenyl)-1,8-diazaspiro[4.5]decane-2,4-dione as a solid. 1H NMR (CDCl3, 400 MHz) δ 7.44 (ddd, J=8.06, 8.06 and 6.23 Hz, 1H); 7.14-7.30 (m, 6H); 6.95 (br d, J=7.88 Hz, 1H); 6.89 (ddd, J=9.16, 2.02, and 2.02 Hz, 1H); 3.52 (s, 2H); 3.26 (s, 2H); 2.73 (m, 2H); 2.65 (m, 2H); 1.85 (br m, 4H). Electrospray mass spectrum M+H=353.1

Provenance & Evidence