Hydrochloric Acid → (R)-1-(6-azido-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

To a solution of (S)-2,2,2-trifluoro-1-(6-hydroxy-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)ethanone (3.0 g, 10 mmol) in 30 mL of toluene at −10° C. was added DPPA (2.6 mL, 12 mmol). To this stirred solution was then added DBU (1.8 mL, 12 mmol) dropwise while keeping the temperature below 0° C. After stirring at room temperature overnight, 7 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 100:20) to afford (R)-1-(6-azido-3,4,6,7,8,9-hexahydrobenzo[g]-isoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone as a colorless oil which was directly used in the next step.

1. customthe temperature below 0° C
2. customthe resulting solution was evaporated to dryness

ORD-Eintrag

ord-ac7f942174e34f35bbf3cd44f310aadc

Quelldatensatz

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07662811B2