Triethylamine → 2-(4-(4-Phenylbenzoylamino)butyl)-7-(3-pyridyl)sulfonyloxy-1,2,3,4-tetrahydroisoquinoline

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Reaction Steps

To a stored solution of 7-hydroxy-N-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline (05 g, 1.3 mmol) and triethylamine (0.21 ml; 1.5 mmol) in dichloromethane (20 ml) was added pyridine-3-sulfonyl chloride (0.25 g, 1.4 mmol). The mixture was stirred for 18 h, then partitioned between dichloromethane (4×30 ml) and saturated aqueous NaHCO3 (100 ml). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography on silica using 0-5% methanolethyl acetate gradient elution gave the title compound (0.06 g, 12%) as an oil.

Provenance & Evidence