Acetic Acid → 1-(1,4-Dioxaspiro[4.5]decan-8-yl)-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

A solution of compound 1 (0.2 g, 1.502 mmol) and compound 2 (0.28 g, 1.802 mmol) in dry 1,2-dichloroethane (5 mL) was treated with acetic acid (0.085 mL, 1.502 mmol) followed by sodium triacetoxyborohydride (0.38 g, 1.802 mmol) at 0° C. The resulting mixture was brought to room temperature and stirred for 3 h. The reaction was basified with 1 N NaOH solution (20 mL) and the product was extracted into ethyl acetate (2×20 mL). The combined ethyl acetate layer was washed with brine (15 mL) and dried (Na2SO4). The solvent was evaporated and the crude product was purified by column chromatography (ethyl acetate:hexanes, 1:4) to obtain compound 3 (0.22 g, 53.6%) as a syrup. 1H NMR (CDCl3) δ 7.06 (t, 1H, J=7.8 Hz), 6.95 (d, 1H, J=7.2 Hz), 6.67-6.55 (m, 2H), 3.96 (s, 4H), 3.72-3.63 (m, 1H), 3.21 (t, 2H, J=5.4 Hz), 2.72 (t, 2H, J=6.3 Hz), 1.92-1.63 (m, 10H); ESI-MS (m/z, %) 274 (MH+, 100).

Provenance & Evidence