Br.[C@H:2]12[CH2:8][C@H:5]([NH:6][CH2:7]1)[CH2:4][S:3]2(=[O:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][Cl:20].O>CN(C=O)C.CCOC(C)=O>[Cl:20][CH2:19][CH2:18][N:6]1[CH2:7][C@@H:2]2[CH2:8][C@H:5]1[CH2:4][S:3]2(=[O:10])=[O:9]To a solution of (1S,4S)-2-thia-5-azabicyclo[2.2.1]heptane 2,2-dioxide, hydrobromide (0.5 g, 2.192 mmol) in DMF (25 mL) was added potassium carbonate (0.397 mL, 6.58 mmol) followed by 1-bromo-2-chloroethane (0.927 mL, 10.96 mmol). The reaction mixture was stirred at rt. After 30 h, the reaction mixture was poured into water (20 mL) and extracted with EtOAc (2×50 mL). The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated to viscous light brown oil. The crude material was loaded onto a silica gel column, eluted with 1:2 hex:EtOAc to give (1S,4S)-5-(2-chloroethyl)-2-thia-5-azabicyclo[2.2.1]heptane 2,2-dioxide (150 mg, 32.6% yield) of a clear glass material. LC/MS: m/e 210.0 (M+H)+, 0.240 min (method 3).
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