Diisobutylaluminum hydride → 1-Boc-2-Formylpyrrolidine

Temperature

-78 °C

To a solution of 1-tert-butyl 2-methylpyrrolidine-1,2-dicarboxylate (3.5 g, 15.3 mmol) in toluene at −78° C. was added DIBAL-H (17.6 mL, 30 mmol, 1.7 M) dropwise while maintaining the reaction temperature below −65° C. The reaction was stirred at −78° C. for 2 h and then quenched with methanol (10 mL). The mixture was then diluted with ethyl acetate (50 mL), saturated NH4Cl was added, and the mixture was stirred vigorously for 20 min at room temperature. The two phases were then separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organics were then washed with brine, dried over Na2SO4, concentrated under reduced pressure and purified by column chromatography to give 3 g of the desired product. MS (ESI): 200 (MH+).

1. temperaturewhile maintaining the reaction temperature below −65° C
2. customquenched with methanol (10 mL)
3. additionThe mixture was then diluted with ethyl acetate (50 mL), saturated NH4Cl
4. additionwas added
5. stirringthe mixture was stirred vigorously for 20 min at room temperature
6. customThe two phases were then separated
7. extractionthe aqueous layer was extracted with DCM (2×50 mL)
8. washThe combined organics were then washed with brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated under reduced pressure
11. custompurified by column chromatography

ORD record

ord-5d574bf8ae7343e7989aa8a4195317cf

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772301B2