Ethanol → HCID 67054558, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-(4′-Chloro-biphenyl-2-yl)-ethanone (2.42 g, 10.5 mmol) and 4-piperidone ethylene ketal (1.50 g, 10.5 mmol) and titanium (IV) isopropoxide (5.96 g, 21.0 mmol) is heated up to 75° C. for 3 hours. The reaction is then cooled to room temperature and is added 50 mL of ethanol followed by sodium borohydride (1.19 g, 31.5 mmol) the reaction is then stirred for 18 hours at room temperature and then quench with 50 mL of methanol. The crude reaction is then dissolved in ethyl acetate and then washed with a saturated solution of sodium bicarbonate. The aqueous layer is then extracted 2 times with ethyl acetate. The combined organic layer are then dried on MgSO4 and the solvent is removed under vacuum. The residue is chromatographed on silica gel gel (gradient: heptane/EtOAc; 0 to 60% EtOAc over 15 minutes) to afford 8-[1-(4′-Chloro-biphenyl-2-yl)-ethyl]-1,4-dioxa-8-aza-spiro[4.5]decane (3.6 g, 96%). Found m/z ES+=358.5 (M+H); 1H NMR (400 MHz, CD2Cl2) δ 7.64 (1H, d, J=8.1 Hz), 7.41 (2H, d, J=8.6 Hz), 7.40 (1H, t), 7.30 (2H, J=8.6 Hz), 7.29 (1H, t), 7.18 (1H, d, J=7.6 Hz), 3.90 (4H, s), 3.51 (1H, m), 2.48 (2H, m), 2.36 (2H, m), 1.62 (4H, m), 1.27 (3H, d, J=6.6 Hz).

Provenance & Evidence