3,4-dihydro-2H-pyran → 2-Tetrahydropyranyl 4-benzyloxycarbonylaminobicyclo[2,2,2]octane-1-carboxylate

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Reaction Steps

4-Benzyloxycarbonylaminobicyclo[2,2,2]octane-1-carboxylic acid (1.00 g) was suspended in dichloromethane (10 mL). To this suspension, 3,4-dihydro-2H-pyran (1.20 mL) and then p-toluenesulfonic acid monohydrate (6.3 mg) were added and the mixture was stirred at room temperature for 30 minutes. Subsequently, the reaction mixture was sequentially washed with a saturated aqueous sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=4:1) to give 2-tetrahydropyranyl 4-benzyloxycarbonylaminobicyclo[2,2,2]octane-1-carboxylate (1.18 g).

Provenance & Evidence