Triacetoxyperiodinane → HCID 57692751, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) suspension of N5-(2-hydroxypropyl)-N1,N1-diisopropyl-3-phenyl-2-pyridin-3-ylpentanediamide (20 mg, 0.047 mmol) in 1 mL dry CH2Cl2 was added solid Dess-Martin periodinane (24 mg, 0.056 mmol), and the reaction was stirred at 0° C. for 3.5 h. The cooling bath was then removed and stirred at room temperature for 1.5 h. More Dess-Martin periodinane was added (two 24 mg portions in 1.5 h interval). The reaction was quenched with saturated aqueous NaHCO3: saturated aqueous Na2S2O3 (1:1 v/v) and partitioned between CH2Cl2 and saturated aqueous NaHCO3. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give a white solid. This material was used directly in the next step.

Provenance & Evidence