Diisobutylaluminum hydride → 1-Boc-2-Formylpyrrolidine

Participants

Reaction Conditions

Reaction Steps

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+).

Provenance & Evidence