1-Boc-3-pyrrolidinol → Tert-butyl 3-oxopyrrolidine-1-carboxylate

Participants

Reaction Steps

N-Boc-3-pyrrolodinol (17.192 g, 0.092 mole) in 50 mL anhydrous methylene chloride was added to a solution of (60 g, 0.276 mole) of pyridinechlorochromate in 300 mL anhydrous methylene chloride which was surrounded by a water bath at room temperature. After stirring at room temperature for 4 hours an additional (60 g, 0.276 mole) of pyridinechlorochromate was added and the reaction was stirred over night. The reaction had gone to completion by the next morning and was diluted with 400 mL diethyl ether and filtered through a pad of celite 521 filter aid using excess diethyl ether to wash through. Evaporation gave a black oil which was flash chromatographed over silica gel eluting with 40% ethyl acetate in hexane to provide the title compound (12.5 g, 71%) as an oil. Mass Spec FD+MI=184.9, (MW=185) 1H NMR (300 MHz CDCl3) δ 1.49 (9H, s); 2.56-2.61 (2H, t); 3.75-3.80 (4H, t).

Provenance & Evidence