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

Participants

Reaction Conditions

Reaction Steps

Chlorocyclooctadiene rhodium(I) dimer (29.2 mg, 0.118 mmol of Rh), Josiphos SL-J216-2 (79.1 mg, 0.123 mmol), and N-(1-(3-chlorobenzyl)-7-methoxy-3,4-dihydronaphthalen-2-yl)propionamide (43.30 g, 122 mmol) were combined in a metal reactor, and the vessel was inerted with argon. Degassed methanol (435 ml) was added, then the mixture was agitated under argon at 45° C. for 20 min. The reactor was pressurized to 60 psig with hydrogen and agitated at 60° C. for 16 hrs. HPLC analysis showed complete conversion and 95.2% ee. The mixture was concentrated, and the resulting solid was slurried in heptane and dried in vacuo at 40° C. to yield 42.8 g (yield: 95%) of the title compound.

Provenance & Evidence