CID 71433830 → N-((1R,2S)-1-(3-fluorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide

Participants

Reaction Conditions

Reaction Steps

Chlorocyclooctadiene rhodium(I) dimer (0.165 g, 0.669 mmol of Rh), Josiphos SL-J216-2 (0.451 g, 0.702 mmol), and N-(1-(3-fluorobenzyl)-7-methoxy-3,4-dihydronaphthalen-2-yl)propionamide (45.4 g, 134 mmol) were combined in a metal reactor, and the vessel was inerted with argon. Degassed methanol (223 ml) was added, and the reactor was agitated under argon for 20 min at 50° C. The reactor was pressurized with 60 psig of hydrogen and stirred at 60° C. for 30 hrs. HPLC analysis indicated complete conversion and 95.2% ee. The mixture was concentrated, filtered in EtOAc through silica gel, concentrated, slurried in hot heptane, filtered, and dried to yield 39.6 g (yield: 87%) of the title compound.

Provenance & Evidence