Tetrahydrofuran → HCID 57803521, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5,7,8-trimethyl-4-oxo-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-yl acetate (2 g), Znl2 (100 mg) and trimethylsilyl cyanide (4 mL) was stirred at 70° C. for 2 h. A homogeneous solution was obtained. The solution was cooled down to room temperature, and THF (30 mL) was added, followed by 1 g of lithium aluminum hydride. After stirring at 60° C. for 3 h, the solution was cooled down and EtOAc was added to destroy excess lithium aluminum hydride. The mixture was poured into water and extracted with EtOAc. The EtOAc was washed with water and dried. After evaporation a white solid was obtained (1 g), which was washed with DCM to give 4-(aminomethyl)-5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-4,6-diol. 1H-NMR (300 MHz, CDCl3+CD3OD): δ=2.85 (AB, J=13.44 Hz, 2H), 2.36 (s, 2H), 2.35-1.60 (m, 6H), 2.11 (s, 9H) ppm. 13C-NMR (75 MHz, CDCl3+CD3OD) δ=146.82, 145.54, 124.91, 123.75, 121.01, 120.48, 76.49, 75.64, 50.07, 44.97, 34.46, 32.36, 13.75, 13.31, 12.50, 12.22 ppm. MS: (m/z)=260 (M+−OH).

Provenance & Evidence