Diisobutylaluminum hydride → 1-(2,2-Dimethylpropyl)-5-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

Ethyl (1R,2R)-2-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclopropanecarboxylate (31-3, 126 mg, 0.38 mmol, 1.0 equiv) was added to anhydrous THF (3.8 mL) and cooled to 0° C. DIBAL-H (1.9 mL, 1.90 mmol, 5.0 equiv, 1.0M in THF) was added dropwise and the resulting solution was stirred at 0° C. for 2 h. The reaction was then quenched by the addition of saturated Rochelle salts (20 mL), diluted with EtOAc (10 mL) and stirred at RT for 18 h. Following this duration, the layers were separated and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give a clear, yellow oil. Purification by reverse-phase HPLC (10-100% 0.1% TFA in 1-120:CH3CN) provided 31-4 as a colorless oil.

Provenance & Evidence