Hydrochloric Acid → 7',8'-dimethyl-2',3'-dihydro-1'H-spiro[cyclobutane-1,4'-quinolin]-6'-ol

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Reaction Steps

A solution of 6′-hydroxy-7′,8′-dimethyl-1′H-spiro[cyclobutane-1,4′-quinolin]-2′(3′H)-one (4.6 g) in THF was added to BH3-THF (45 mL) at 0° C. The mixture was stirred at room temperature for 20 minutes and allowed to reflux overnight. The mixture was cooled down and at 0° C., 3 N HCl was added to quench the excess BH3. The solvent was removed by evaporation. The solid present was collected by filtration and washed with hexane (×3), giving 7′,8′-dimethyl-2′,3′-dihydro-1′H-spiro[cyclobutane-1,4′-quinolin]-6′-ol (700 mg) as a light yellow solid. 1H-NMR (300 MHz, CDCl3) δ=6.54 (s, 2H); 4.21 (t, J=6 Hz, 2H); 2.15 (m, 5H); 2.02 (m, 8H); 2.19 (m, 8H); 1.94 (t, J=6 Hz, 2H) ppm. MS: (m/z)=218 (100, M+H+).

Provenance & Evidence