CID 71433830 → N-((1R,2S)-1-benzyl-6-fluoro-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide

Participants

Reaction Conditions

Reaction Steps

Chlorocyclooctadiene rhodium(I) dimer (0.648 g, 2.63 mmol of Rh), Josiphos SL-J216-2 (1.779 g, 2.77 mmol), and N-(1-benzyl-6-fluoro-7-methoxy-3,4-dihydronaphthalen-2-yl)propionamide (93.96 g, 277 mmol) were combined in a metal reactor, and the vessel was inerted with argon. Degassed methanol (940 ml) was added, and the mixture was agitated under 20 psi of argon at 50° C. for 20 min. The vessel was pressurized with 60 psig of hydrogen and agitated at 55° C. for 14 hrs. HPLC analysis indicated complete conversion and 94.7% ee. The mixture was concentrated, and the resulting solid was precipitated from MeOH to yield 86.9 g (yield: 92%) of the title compound.

Provenance & Evidence