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

HRID 1614346Notes

Reaction equation

HRID 1614346 reaction equation
C1(C)C=CC(S([N:10]2[CH2:15][C@@H:14]3[CH2:16][C@H:11]2[CH2:12][N:13]3[CH3:17])(=O)=O)=CC=1.[BrH:19]>C(O)(=O)C>[BrH:19].[BrH:19].[CH3:17][N:13]1[CH2:12][C@@H:11]2[CH2:16][C@H:14]1[CH2:15][NH:10]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 11054620(1S,4S)-2-Methyl-5-tosyl-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 15629279(1S)-2-methyl-2,5-diazobicyclo[2.2.1]heptane dihydrobromideYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

60 g (225 mmol) of (1S, 4S)-2-(4-Toluenesulfonyl)-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)

Workup

  1. customAfter 6 hours the acetic acid was removed under aspirator pressure to 1/4 of the original volume and 1800 ml of ethylacetate
  2. additionwas then added
  3. customA solid precipitated
  4. filtrationwas filtered under an inert atmosphere
  5. customThe product was recrystallized
  6. dissolutionby dissolving in a minimum amount of methanol
  7. temperatureat reflux
  8. temperatureCooling
  9. additionfollowed by the addition of 400 ml of isopropyl alcohol
  10. customprovided a white solid which
  11. filtrationwas filtered
  12. customdried under reduced pressure
  13. customM.P.=258°-259° C. (coloration occurs at 234° C.)
  14. custom[α]D =+13.21° (c=0.946, CH3OH)

Sources & evidence

ORD record
ord-f7bffaca204b4c22a0ebcd10eaf73614
Source dataset
uspto-grants-1993_03
Patent number
US05196548

Reaction notes

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