Succinic anhydride → 4-(7-fluoro-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)-4-oxobutyric acid

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Reaction Steps

5.0 g (49.7 mmol) of succinic anhydride and 4.0 ml (28.4 mmol) of NEt3 were added in succession to a solution of the crude product 7-fluoro-1-phenyl-1,2,3,4-tetrahydroisoquinoline (max. 14.2 mmol) in MeCN (200 ml) and the mixture was stirred for 16 h at RT. It was then concentrated to small volume under vacuum and the residue was taken up with a saturated aqueous NaHCO3 solution (300 ml). It was extracted with DCM (2×200 ml). The combined organic phases were washed with a 1M aqueous hydrochloric acid (200 ml), dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (heptane/EE 1:1+1% AcOH) of the residue produced 1.72 g (5.3 mmol, 10% over 3 stages) of 4-(7-fluoro-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)-4-oxobutyric acid.

Provenance & Evidence