Hexane → HCID 18657882, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of propargyl 2-tetrahydropyranyl ether (15.2 g, 109 mmol) in tetrahydrofuran (165 ml), 1.6 N n-butyllithium in hexane (68.1 ml, 109 mmol) was added in a nitrogen stream under cooling with ice, and the mixture was stirred under cooling with ice for 1 hour. The mixture was cooled to -78° C. and added to a solution of (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyl-dimethylsiloxy-2-formylpyrrolidine (31.7 g, 90.2 mmol in tetrahydrofuran (150 ml) obtained by Reference Example 1-3) in a nitrogen stream at -78° C. and the mixture was stirred for 1 hour at the same temperature. After the reaction mixture was raised to -20° C. and stirred at the same temperature for 1.5 hours, a saturated ammonium chloride aqueous solution (150 ml) was added thereto and stirred. Ethyl acetate was added hereto and the organic layer was washed with water a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (Wakogel™ C-300, hexane-ethyl acetate 1:1) to obtain (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[1-hydroxy-4-(2-tetrahydropyranyloxy)-2-butynyl]pyrrolidine (38.2 g, yield: 90%).

Provenance & Evidence