Methanol → HCID 23649128, compound

Participants

Reaction Steps

A solution of N,N-dimethyl-2H-spiro[naphthalene-1,4′-piperidine]-4-carboxamide (B3) (33 mg, 0.13 mmol) and ethyl 4-oxopiperidine-1-carboxylate (60 mg, 0.35 mmol) in 1,2-dichloroethane (2 ml) was stirred at 40° C. for 5 h, followed by addition of titanium (IV) isopropoxide (0.05 ml, 0.17 mmol). The reaction mixture was stirred for 18 h and treated with sodium triacetoxyborohydride (50 mg, 0.23 mmol) for 24 h. Methanol (1 ml) was added and the reaction mixture was stirred for 1 h, evaporated and the residue was dissolved in methanol (1 ml) and purified by C-18 HPLC to give ethyl 4-(4-(dimethylcarbamoyl)-2H-spiro[naphthalene-1,4′-piperidine]-1′-yl)piperidine-1-carboxylate (Compound No. 4). LC-MS: m/e=426.3 (M+H). Rt=1.55 min. 1H-NMR (500 MHz, DMSO-d6): 9.32 (br. s, 1H), 7.39 (d, 1H), 7.34 (t, 1H), 7.26 (t, 1H), 6.95 (d, 1H), 5.97 (t, 1H), 4.12 (d, 2H), 4.05 (q, 2H), 4.04 (m, 2H), 3.43 (br. d, 2H), 3.22 (q, 2H), 2.98 (s, 3H), 2.81 (s, 3H), 2.80 (m, 1H), 2.56 (d, 2H), 2.14-2.07 (m, 4H), 1.92 (d, 2H), 1.56 (qd, 2H), 1.19 (t, 3H).

Provenance & Evidence