Dimethylformamide → (R)-4-[4-(3-Ethoxymethyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-3,5-diethyl-pyrazol-1-y]-3,5-dimethyl-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of n-butyl lithium (2.5 M hexane solution; 0.043 ml, 0.11 mmol) chilled to -78° C., a solution of (R)-2-[1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-3-ethoxymethyl-1,2,3,4-tetrahydro-isoquinoline (50 mg, 0.098 mmol) in anhydrous tetrahydrofuran (0.2 ml) was added dropwise. After stirring at -78° C. for 10 minutes, anhydrous N,N-dimethylformamide (0.023 ml, 0.29 mmol) was added. The resulting mixture was warmed to ambient temperature and stirred for 1 hour. The reaction quenched by addition of aqueous ammonium chloride (1 ml) and then extracted with ethyl acetate/water (5 ml of each). The separated organic extract was washed with an equal volume solution of aqueous ammonium chloride, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a yellow oil (70 mg). Flash chromatography (silica gel, 40 micron mesh; elution with ethyl actate/hexane=1:4 in volume) afforded the title compound (14 mg) as a faint yellow oil.

Provenance & Evidence