Tetrahydrofuran → HCID 71559418, compound

Participants

Reaction Steps

A mixture of 0.1 g (0.32 mmol) adamantan-1-yl-(4-hydroxy-3,4-dihydro-2H-quinolin-1-yl)-methanone and 35 mg (55% in oil, 0.8 mmol) NaH in 5 mL THF at 0° C. was treated with 0.15 g (0.99 mmol) iododethane and allowed to stir to room temperature and subsequently heated to 50° C. overnight. The mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were dried with MgSO4, filtered and evaporated. The residue was subjected to column chromatography on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 24.5 mg (22%) of the title compound as colourless solid. MS(m/e): 340.3 (MH+).

Provenance & Evidence