Hydrochloric Acid → HCID 67466031, compound

Participants

Reaction Steps

To a solution of tetrahydropyran-4-carboxylic acid 130 mg (1 mmol) in DCM (5 mL) was added 7-bromo-3,4-dihydro-1H-isoquinoline-2-carbaldehyde (200 mg, 1 mmol), followed by TPTU (326 mg) and HOBt (148 mg). The solution was cooled to ice-water bath. To this solution was added ethyl diisopropylamine (0.4 mL). The yellow solution was allowed to stir under nitrogen overnight. LC/MS showed the reaction was complete. The reaction was quenched by addition of sodium bicarbonate solution (5 mL) and DCM (30 mL). The two layers were separated, and the aqueous layer was extracted with DCM (20 mL×2). The combined DCM extracts were washed with sodium bicarbonate (20 mL), and brine (15 mL×2), dried (anhydrous potassium carbonate), filtered, and concentrated in vacuo. The crude product was purified on a silica gel column, eluted with 5-10% MeOH in DCM to get a yellow semi-solid. This was taken in DCM and ether (5 mL) and treated with 0.5 mL of 1N HCl in ether. The white powder was collected and dried to get 0.35 g (100% yield) of the titled compound as a yellow solid.

Provenance & Evidence