Methanol → Benzyl 4-hydroxy-1,2,3,4-tetrahydroquinoline-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a flask were charged 25.04 g of 1-benzyloxycarbonyl-2,3-dihydro-4-quinolone, 6.72 g of sodium borohydride and 200 mL of tetrahydrofuran, and the flask was incubated in a water bath wherein the temperature was maintained constant at 25° C. To the flasks was added dropwise 50 mL of methanol over about 30 minutes with watching out heat generation/foam formation. After confirming the reaction termination by TLC, to the flask was added dropwise 400 mL of water with watching out foam formation, and to the solution was added 800 mL of ethyl acetate and the objective product was extracted. Further, the organic layer was washed with 2.5% saline, and then to the organic layer was added MgSO4, and the insoluble material was filtered. The filtrate was concentrated under reduced pressure to give 24.05 g of 1-benzyloxycarbonyl-4-hydroxy-1,2,3,4-tetrahydroquinoline as white solid (86% yield).

Provenance & Evidence