Hydrochloric Acid → (R)-1-(7-azido-1,2,7,8,9,10-hexahydrobenzo[f]isoquinolin-3(4H)-yl)-2,2,2-trifluoroethanone

Participants

Reaction Steps

To a solution of (S)-2,2,2-trifluoro-1-(7-hydroxy-1,2,7,8,9,10-hexahydrobenzo[f]isoquinolin-3(4H)-yl)ethanone (299 mg, 1 mmol) in 3 mL of toluene at −10° C. was added DPPA (0.26 mL, 1.2 mmol). To this stirred solution was then added DBU (0.18 mL, 1.2 mmol) dropwise while keeping the temperature below 0° C. After stirring at room temperature for 3 h, 0.5 mL of 10% HCl was added and the resulting solution was evaporated to dryness and directly submitted to flash chomatography (SiO2, hexane/EtOAc=100:10 to 100:15 to 100:18) to afford (R)-1-(7-azido-1,2,7,8,9,10-hexahydrobenzo[f]-isoquinolin-3(4H)-yl)-2,2,2-trifluoroethanone as a colorless oil which was directly used in the next step.

Provenance & Evidence