反应详情

To a solution N-BOC-1,3-dihydro-2H-isoindol-1-carboxylic acid, methyl ester (38 mmol) and MeI (10 mL, 160 mmol) in 150 mL of anhydrous THF at −30° C. was added LDA (Aldrich, 1.5 M in cyclohexane, 51 mL, 76.5 mmol). The reaction was allowed to warm up to rt over 4 h. The reaction was cooled to −30° C., and was quenched with saturated aqueous solution of NH4Cl (50 mL). The resulting mixture was partitioned between EtOAc and brine, and the product was extracted with EtOAc (3×100 mL). The combined extracts were dried with anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted with 10:1 to 5:1 hexane/ether to afford N-BOC-1-methyl-1,3-dihydro-2H-isoindol-1-carboxylic acid, methyl ester.

1. temperatureThe reaction was cooled to −30° C.
2. customwas quenched with saturated aqueous solution of NH4Cl (50 mL)
3. customThe resulting mixture was partitioned between EtOAc and brine
4. extractionthe product was extracted with EtOAc (3×100 mL)
5. dry with materialThe combined extracts were dried with anhydrous MgSO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash column chromatography on silica gel
8. washeluted with 10:1 to 5:1 hexane/ether