Acetic Acid → (S)-tert-Butyl 7-(((3S,5S)-1-(tert-butoxycarbonyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)amino)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Participants

Reaction Steps

To a solution of (S)-tert-butyl 4-oxo-2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidine-1-carboxylate (73 mg, 0.20 mmol) in DCE (2.0 mL) was added (S)-tert-butyl 7-amino-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (86 mg, 0.20 mmol) and AcOH (12 μL, 0.20 mmol). Na(OAc)3BH (78 mg, 0.37 mmol) was then added, and the resulting reaction mixture was stirred at room temperature for 4 h. Additional AcOH (12 μL, 0.20 mmol) and Na(OAc)3BH (78 mg, 0.37 mmol) were added, and stirring was continued overnight at room temperature. The reaction mixture was poured into a separatory funnel containing 1N HCl and EtOAc. The aqueous layer was extracted with EtOAc (3×). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (151 mg, 97%) as a colorless oil. MS (ESI+) m/z 764.5 (M+H)+.

Provenance & Evidence