Hydrogen Bromide → (1S)-2-methyl-2,5-diazobicyclo[2.2.1]heptane dihydrobromide

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Reaction Steps

60 g (225 mmol) of (1S, 4S)-2-(4-Toluenesul- fonyl)-5-methyl-2,5-diazabicyclo-[2.2.1]heptane was suspended in 900 ml of 30% hydrogen bromide in acetic acid and the mixture was allowed to stir at room temperature. After 6 hours the acetic acid was removed under aspirator pressure to 1/4 of the original volume and 1800 ml of ethylacetate was then added. A solid precipitated and was filtered under an inert atmosphere. The product was recrystallized by dissolving in a minimum amount of methanol at reflux. Cooling followed by the addition of 400 ml of isopropyl alcohol provided a white solid which was filtered and dried under reduced pressure. The product weighed 48 g which represents an 81% yield. M.P.=258°-259° C. (coloration occurs at 234° C.) [α]D =+13.21° (c=0.946, CH3OH)

Provenance & Evidence