Quinoline → HCID 58128558, compound

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Reaction Steps

The alcohol from step 1 of this example (9.1 g, 24.4 mmol) was dissolved in EtOAc (100 ml) and quinoline (0.48 ml, 4.03 mmol) was added. Lindlar's catalyst (1.04 g) was added and the vessel evacuated and refilled three times with H2. The slurry was stirred under a H2 atmosphere for 40 min. The starting material was completely consumed. The mixture was filtered through CELITE and rinsed with EtOAc (4×50 ml). The volume of EtOAc was reduced ˜80% in vacuum. The remaining solution was diluted with ether (100 ml) and washed with 2N HCl (100 ml). The aqueous fraction was re-extracted with ether (2×50 ml), organics combined and washed with 15 ml 2 N HCl. The organic fraction was washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered, and stripped. The resulting oil was purified by chromatography on SiO2 30% eluting with EtOAc:Hexanes to give the titled compound.

Provenance & Evidence