Hydrogen Bromide → (1S,4S)-2-thia-5-azabicyclo[2.2.1]heptane 2,2-dioxide, hydrobromide
Reaction equation
[C@H:1]12[CH2:17][C@H:4]([N:5](C(OCC3C=CC=CC=3)=O)[CH2:6]1)[CH2:3][S:2]2(=[O:19])=[O:18].[BrH:20]>>[BrH:20].[C@H:1]12[CH2:17][C@H:4]([NH:5][CH2:6]1)[CH2:3][S:2]2(=[O:19])=[O:18]Participants
3
Procedure
(1S,4S)-benzyl 2-thia-5-azabicyclo[2.2.1]heptane-5-carboxylate 2,2-dioxide (1.4 g, 4.98 mmol) was treated with hydrobromic acid (33% in acetic acid) (20 mL, 116 mmol) and stirred at rt. After 18 h, a white precipitate was filtered, washed with glacial acetic acid (5 mL), and dried under reduced pressure to give (1S,4S)-2-thia-5-azabicyclo[2.2.1]heptane 2,2-dioxide, hydrobromide (1.01 g, 85% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.49 (br. s., 2H), 4.60 (br. s., 1H), 4.15 (br. s., 1H), 3.67-3.51 (m, 2H), 3.49-3.32 (m, 2H), 2.34 (d, J=13.2 Hz, 1H). 13C NMR (101 MHz, DMSO-d6) δ 57.7, 56.7, 55.3, 44.2, 33.5.