Acetic Acid → 1'-(4-chlorophenyl)-6'-methoxy-5',7',8'-trimethyl-2',4'-dihydro-1'H-spiro[cyclobutane-1,3'-quinoline]

Participants

Reaction Steps

To a 2 mL mixture of acetic acid and trifluoroacetic acid (1:1, v/v) cooled in ice bath, was added NaBH4 (71 mg) in portions, followed with 1′-(4-chlorophenyl)-6′-methoxy-5′,7′,8′-trimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinolin]-4′-ol (65 mg) in THF (0.5 mL). After 20 min, the mixture was taken up by ethylacetate and water. After separation of the two phases, the aqueous phase was extracted with more ethylacetate, and the combined organic phases were washed with brine, dried and evaporated to yield a thick oil, which was passed through a silica column (EtOAc/Hexane: 0-5% in 30 min) to give 1′-(4-chlorophenyl)-6′-methoxy-5′,7′,8′-trimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline] (34.6 mg). 1H-NMR (300 MHz, CDCl3) δ=7.2-6.933 (d, 2H); 6.783-6.428 (d, 2H); 3.68 (s, 3H); 3.64 (s, 2H); 2.72 (s, 2H); 2.21 (s, 3H); 2.16 (s, 3H); 1.75 (s, 3H); 1.988-1.542 (m, 6H) ppm. 13C-NMR (75 MHz, CDCl3) δ=152.86, 150.26, 136.97, 129.12, 128.7, 128.11, 128.03, 126.65, 123.67, 119.89, 60.78, 60.39, 40.19, 38.65, 32.78, 15.92, 15.51, 13.02, 12.02 ppm.

Provenance & Evidence