Succinic anhydride → HCID 68560648, compound

Participants

Reaction Steps

25.5 g (255 mmol) of succinic anhydride and 20.3 ml (146 mmol) of NEt3 were added in succession to a solution of 16.3 g of the crude product 7-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline from a) in MeCN (300 ml) and the mixture was stirred for 16 h at RT. It was then concentrated to small volume under vacuum. The residue was taken up with DCM (400 ml). It was then washed with a saturated aqueous NaHCO3 solution. The aqueous phase was extracted with DCM (2×400 ml). The collected organic phases were washed with 1N aqueous hydrochloric acid (400 ml) and with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (gradient heptane/EE 1:1 heptane/EE/AcOH 2:2:1) of the residue and subsequent crystallisation of the residue from EE produced 6.79 g (21 mmol, 24% over 2 stages) of 4-(7-methyl-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)-4-oxobutyric acid.

Provenance & Evidence