Cl.[CH:2]12[NH:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH2:5][C:4](=[O:11])[CH2:3]2.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.CCOC(C)=O>CN(C=O)C.CO>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:10]2[CH:6]3[CH2:7][CH2:8][CH2:9][CH:2]2[CH2:3][C:4](=[O:11])[CH2:5]3)(=[O:27])=[O:26])=[CH:21][CH:20]=120.9 g of 9-azabicyclo[3.3.1]nonan-3-one hydrochloride was dissolved in 600 mL of DMF. 89.0 g of Cs2CO3 followed by 29 g of 4-chlorobenzenesulfonyl chloride was added and the reaction mixture was stirred overnight at rt. After an additional day of stirring, the reaction mixture was poured into 1.4 L of vigorously stirring EtOAc. The mixture was stirred for 2 h and allowed to stand at rt overnight. The mixture was filtered to remove undissolved solids and the filtrate was washed with H2O (2 L×3) and brine (2 L). The organic layer was dried over MgSO4, filtered and the solvent was removed by rotary evaporation. A granular, tan solid was produced. Trituration with methanol dissolved a tan impurity to afford 9-(4-chlorophenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one as a white crystalline solid (25.9 g, 69% yield).
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