Triacetoxyperiodinane → HCID 59765016, compound

Participants

Reaction Steps

To a solution of ((2S,4R)-4-hydroxy-2-isopropyl-pyrrolidin-1-yl)-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridin-6-yl)-methanone (prepared as in example #1) (0.118 g, 0.330 mmol) in DCM (4 mL) was added Dess-Martin periodinane (0.210 g, 0.495 mmol). The reaction mixture was stirred at ambient temperature for about 40 min. Additional Dess-Martin reagent (0.303 g, 0.714 mmol) was added in portions over about 4 h and the reaction mixture was stirred for about 16 h. Saturated aqueous sodium bicarbonate (4 mL) was added and the organic portion was separated, dried over MgSO4, filtered, and concentrated to afford (S)-5-isopropyl-1-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridine-6-carbonyl)-pyrrolidin-3-one as a sticky yellow solid that was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method d) Rt 2.49 min; m/z: (M+H)+ 356.

Provenance & Evidence