HCID 21180664, compound → HCID 21180827, compound

Participants

Reaction Steps

A mixture of 430 mg (1.0 mmol) of 1-benzyl-4-(3-phenyl-2,2-bis(carboethoxy)propyl)piperidine (from EXAMPLE 32, Step D) and 65 mg (1.7 mmol) of lithium aluminum hydride was heated at reflux for 1 h. The reaction was cooled and quenched with 10 mL of 1.0 N NaOH. The quenched mixture was partitioned between 50 mL of ether and 25 mL of H2O and the layers were separated. The organic layer was dried over MgSO4 and concentrated. The resulting solid was triturated with ether, filtered and dried to afford 204 mg (59%) of the title compound: 1H NMR (500 MHz) δ 1.16 (d, J=5.0,2H), 1.32-1.36 (m, 2H), 1.45-1.49 (m, 1H), 1.66 (d, J=12.0, 2H), 1.76 (br s, 2H), 1.97 (app t, J=11.5, 2H), 2.40 (br s, 2H), 2.73 (s, 2H), 2.83 (app d, J=11.5, 2H), 3.48 (s, 2H), 3.58 (ABq, J=10.5, 4H), 7.19-7.31 (10H).

Provenance & Evidence