[N+](C1C=CC(S([N:13]2[C:17]3([CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:16][CH2:15][CH:14]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=O)=O)=CC=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.C1(S)C=CC=CC=1>C(#N)C>[NH:13]1[C:17]2([CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[CH2:16][CH2:15][CH:14]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]
To a solution of ethyl 1-[(4-nitrophenyl)sulfonyl]-8-oxa-1-azaspiro[4.5]decane-2-carboxylate (165) (1.47 g, 3.7 mmol) in anhydrous acetonitrile (25 mL) was added potassium carbonate (0.76 g, 5.5 mmol), 18-crown-6 (0.2 g, 0.7 mmol) and thiophenol (0.6 mL. 5.5 mmol) and the reaction stirred at room temperature for 18 h. The reaction was concentrated in vacuo and the residue dissolved in 0.1 N HCl. The aqueous layer was extracted twice with EtOAc and the organic layer was discarded. The aqueous layer was treated with solid potassium carbonate until the solution gave blue pH paper. It was extracted with 15% isopropanol/dichloromethane (3×) and the organic layer dried over sodium sulfate and concentrated in vacuo to afford the title compound as a clear oil (0.71 g, 90% yield).
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