Ethyl 2-oxo-4-oxa-8-azaspiro[4.5]decane-8-carboxylate → Ethyl 3-hydroxy-3-(2-phenylethynyl)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

Participants

Reaction Steps

To a solution of ethyl 2-oxo-4-oxa-8-azaspiro[4.5]decane-8-carboxylate (Edwin S. C. Wu, Ronald C. Griffith, James T. Loch III, Alex Kover, Robert J. Murray, George B. Mullen, James C. Blosser, Anthony C. Machulskis, Sally A. McCreedy, J. Med. Chem., 1995, 38 (9), pp 1558-1570, 82 mg, 0.362 mmol) in THF (4 mL) was added dropwise a 1M solution of phenylethynylmagnesium bromide in THF (0.724 mL, 0.724 mmol), stirring at r.t. under anhydrous nitrogen atmosphere. The reaction mixture was stirred at r.t. for 4 h, then at 60° C. for 6 h, then it was quenched with a saturated aqueous solution of ammonium chloride, extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulphate and evaporated to dryness in vacuo. The crude was purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum Ether-EtOAc from 75:25 to 4:6) affording the title product as yellow solid. Yield: 87.2%.

Provenance & Evidence