Tetrahydrofuran → HCID 67536727, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.64 M tert-butyllithium in n-pentane (12 mL) was added to a mixture of 2-(2,2-dimethylpropanoyl)-1,2,3,4-tetrahydroisoquinoline (3.0 g), tetramethylethylenediamine (2.2 ml), and THF (40 mL) at −78° C. The reaction liquid was stirred at −78° C. for 10 minutes. Then, acetone (1.8 mL) was further added to the liquid at −78° C., followed by stirring at −78° C. for 1 hour. Acetic acid (2 mL) was added to the reaction liquid, and the temperature was raised to room temperature. The reaction liquid was evaporated under reduced pressure. EtOAc and water were added thereto, followed by liquid separation. The organic layer was washed sequentially with an aqueous 5% citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 2-[2-(2,2-dimethylpropanoyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]propan-2-ol (2.62 g).

Provenance & Evidence