CID 71433830 → N-((1R,2S)-1-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Chlorocyclooctadiene rhodium(I) dimer (3.70 mg, 15.0 μmol of Rh), Josiphos SL-J216-2 (10.16 mg, 16.0 μmol), and N-(1-benzyl-7-methoxy-3,4-dihydronaphthalen-2-yl)pyrrolidin-2-one (500.8 mg, 1.50 mmol) were combined in a glass-lined metal reactor, and the vessel was inerted with argon. Degassed methanol (5.0 ml) was added, and the mixture was agitated under 20 psi of argon at 50° C. for 20 min. The vessel was pressurized with 90 psig of hydrogen and stirred at 100° C. for 45 hrs. HPLC analysis indicated 99.8% conversion and 90.7% ee. The mixture was concentrated and diluted with water to yield 415 mg (yield: 82%) of the title compound.

Provenance & Evidence