Hydrochloric Acid → HCID 11694753, compound

Participants

Reaction Steps

To a solution of 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutane]-3-carbaldehyde O-methyloxime (150 mg) in 10 mL of THF at 0° C. was added BH3/pyridine complex (2.27 mL). Subsequently, 9 mL of HCl in dioxane (4.0 M solution) was added over a period of 1 hour. The reaction mixture was allowed to stir overnight. The mixture was extracted with ethyl acetate, washed with saturated NaHCO3, and concentrated in vacuo. The residue was purified by flash chromatography eluted with 30% ethyl acetate in hexane to give 142 mg of 3-[(methoxyamino)methyl]-5,7-dimethylspiro[chromene-2,1′-cyclobutan]-6-ol as a yellow solid. 1H-NMR (300 MHz, CDCl3) δ=6.59 (s, 1H, =CH), 6.45 (s, 1H), 5.50 (b, 1H), 4.75 (b, 1H), 3.81 (s, 2H), 3.62 (s, 3H), 2.20 (s, 3H), 2.19 (s, 3H), 2.40-1.75 (m, 6H) ppm. 13C-NMR (75 MHz, CDCl3) δ=146.3, 146.0, 134.0, 123.9, 120.3, 119.4, 119.1, 114.6, 81.1, 62.0, 54.7, 33.1, 16.5, 14.3, 11.2 ppm. MS: (m/z)=229.1 (M−NH2OMe+).

Provenance & Evidence