4-Toluenesulfonyl chloride → Tert-butyl 3-(benzyloxy)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

Participants

Reaction Steps

4.81 g of tert-butyl 4-[2-(benzyloxy)-3-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate was dissolved in 20 ml pyridine, 2.76 g of tosyl chloride was added thereto, and the mixture was stirred at room temperature for 2 hr. Further, 1.00 g of tosyl chloride was added thereto, and the mixture was stirred at room temperature for 30 min, and at 50° C. for 35 min. The reaction solution was partitioned into ethyl acetate and water, washed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate and brine, and dried over magnesium sulfate. After filtration, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 3.72 g of tert-butyl 3-(benzyloxy)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate.

Provenance & Evidence