反应详情

At −78° C. to a solution of 2-benzyl 1-tert-butyl 4-iodo-1H-pyrrole-1,2-dicarboxylate (10.0 g, 23.4 mmol), and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.6 mL, 47 mmol) in THF (120 mL) was added dropwise a solution of 2.5 M n-butyllithium in hexane (11.2 mL, 28.1 mmol) with stirring. After completion of addition the mixture was stirred at this temperature for 35 min and then 2.5 M n-butyllithium in hexane (1.87 mL, 4.68 mmol) was added and stirred for another 30 minutes. The reaction was quenched with sat. NH4Cl solution and then diluted with EtOAc. The organic layer was separated, washed with water twice, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The product was isolated by chromatography eluting with 0 to 10% EtOAc in hexanes. LCMS calculated for C19H23BNO6 (M−[tBu+1]+1)+: m/z=372.2. found: 372.2.

1. additionAfter completion of addition the mixture
2. stirringwas stirred at this temperature for 35 min
3. stirringstirred for another 30 minutes
4. customThe reaction was quenched with sat. NH4Cl solution
5. additiondiluted with EtOAc
6. customThe organic layer was separated
7. washwashed with water twice
8. washwashed with brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated under reduced pressure
11. customThe product was isolated by chromatography
12. washeluting with 0 to 10% EtOAc in hexanes