反应详情

温度

100 °C

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)+.

1. additionpoured into a sep funnel
2. extractionThe aqueous layer was extracted with EtOAc (3×)
3. washThe combined organic extracts were washed with sat. NaCl
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a crude oil
8. customPurification
9. washflash column chromatography (gradient elution from 0 to 100% EtOAc/hexanes)