Sodium Carbonate → (S)-tert-Butyl 7-((S)-1-((benzyloxy)carbonyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-2,5-dihydro-1H-pyrrol-3-yl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-benzyl 2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-4-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylate (226 mg, 0.43 mmol), (S)-tert-butyl 3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (229 mg, 0.43 mmol) and 2M aq. Na2CO3 (540 μL, 1.08 mmol) in dioxane (4.3 mL) was degassed with argon. Pd(Ph3P)4 (50 mg, 0.043 mmol) was added, and the reaction mixture was stirred at 100° C. for 2 h and then poured into a sep funnel containing sat. NH4Cl. The aqueous layer was extracted with EtOAc (3×). The combined organic extracts were washed with sat. NaCl, dried over Na2SO4, filtered and concentrated in vacuo to give a crude oil. Purification using flash column chromatography (gradient elution from 0 to 100% EtOAc/hexanes) provided the title compound (265 mg, 79%) as a colorless oil. MS (ESI+) m/z 781.2 (M+H)+.

Provenance & Evidence