Iodoethane → HCID 18657889, compound

Participants

Reaction Steps

To a solution of (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(2-pyrrolidon-4-yl)pyrrolidine (38.5 g, 0.1 mol, the compound of Reference Example 1-6) in tetrahydrofuran (200 ml) was added 60% sodium hydride in oil (4.2 g, 0.1 mol) under ice-cooling, and the mixture was stirred for 1 hour. To the mixture was added ethyl iodide (8 rag, 0.1 mol), and after stirring at room temperature overnight, the reaction mixture was concentrated. The residue was extracted with ethyl acetate (500 ml), and the mixture was washed with water (200 ml) followed by a saturated sodium chloride aqueous solution. After the extract was dried over anhydrous magnesium sulfate, the solvent was removed in vacuo, and the residue was purified by silica gel column chromatography (Wakogel™ C-300, chloroform) to obtain (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(N-ethyl-2-pyrrolidon-4-yl)pyrrolidine (40.3 g, yield: 97.7%).

Provenance & Evidence