Norcamphor → 1'-(bicyclo[2.2.1]heptan-2-yl)-N-methylspiro[indene-1,4'-piperidine]-3-carboxamide

Participants

Reaction Steps

A mixture of (C6) (0.015 g, 0.073 mmol), titanium (IV) isopropoxide (0.065 mL, 0.22 mmol) and (1R,4S)-bicyclo[2.2.1]heptan-2-one (3 eq) was stirred at room temperature for 18 h in dichloroethane (0.5 mL). Sodium triacetoxyborohydride (0.013 g, 0.073 mmol) was added and the reaction stirred at room temperature for 1 h. The solvent was evaporated and 6N NaOH (0.5 mL) and methanol (1 mL) was added and triturated to give a white solid. The solid was washed with methanol (1 mL) and EtOAc (1 mL). The filtrate was concentrated under reduced pressure to afford the crude product that was purified by reverse phase preparative HPLC to afford 1′-(bicyclo[2.2.1]heptan-2-yl)-N-methylspiro[indene-1,4′-piperidine]-3-carboxamide (Compound No. 38) (0.012 g) as an oil. LC/MS (10-90% over 3 min with 0.9% FA) m/z 337.2 (M+1), Rt 1.7 minutes. 1HNMR (500 MHz, CD3OD): δ 7.74 (d, 1H), 7.35 (m, 4H), 3.73 (m, 2H), 3.55 (m, 1H), 3.30 (m, 2H), 2.91 (s, 3H), 2.42-2.74 (m, 5H), 2.19 (m, 2H), 1.54-1.74 (m, 8H), 1.31 (m, 1H)

Provenance & Evidence