Isopropyl iodide → HCID 57424222, compound

Participants

Reaction Steps

Following General Procedure C and using 8-formyl-2,2,4,4-tetramethyl-chroman-6-carboxylic acid ethyl ester (Intermediate 37, 0.11 g, 0.23 mmol) in dichloromethane (4 mL) and acetonitrile (2 mL), cyclopropyl amine (0.08 mL, 1.1 mmol), acetic acid (0.8 mL) and sodium cyanoborohydride (0.072 g, 1.1 mmol) followed by work up and flash column chromatography afforded an intermediate. The intermediate (0.122 g, 0.22 mmol) was dissolved in acetone (10 mL) and treated with potassium carbonate (0.153 g, 1.1 mmol) and isopropyl iodide (0.04 mL). The resulting reaction mixture was at 60° C. for 4 h. The volatiles were evaporated in vacuo, the residue was diluted with water and extracted with ethyl acetate. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. Flash column chromatography over silica gel (230-400 mesh) using 15-20% ethyl acetate in hexane as the eluent afforded the title compound (0.09 g, 71%) as a clear oil.

Provenance & Evidence