Potassium Carbonate → HCID 19887570, compound

HRID 654526Notes

Reaction equation

HRID 654526 reaction equation
[Br-].C([N+:9]12[CH2:16][C:13]([C:17]([O:19][CH2:20]C)=[O:18])([CH2:14][CH2:15]1)[CH2:12][CH2:11][CH2:10]2)C1C=CC=CC=1.[H][H].[C:24](=[O:27])([O-:26])[O-].[K+].[K+]>C(O)C.Cl.[Pd]>[C:17]([OH:19])(=[O:18])[C:24]([OH:26])=[O:27].[N:9]12[CH2:16][C:13]([C:17]([O:19][CH3:20])=[O:18])([CH2:14][CH2:15]1)[CH2:12][CH2:11][CH2:10]2

Participants

7

Reactant 3

HCID 11430Potassium Carbonate2×HCID 19887576HCID 19887576, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19887570HCID 19887570, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent3×HCID 702EthanolSolvent

Procedure

A solution of the crude ethyl 1-benzyl-1-azoniabicyclo[3.2.1]oct-5-ylcarboxylate bromide (D4) in ethanol (200 ml) and 11M hydrochloric acid (5 ml), was hydrogenated over 10% Pd-C (1 0 g) at atmospheric pressure and 40° C. until the uptake of hydrogen was complete. The catalyst was filtered off through kieselguhr and the filtrate concentrated in vacuo to leave a yellow semi-solid, which was treated with 8M hydrochloric acid (150 ml) and heated under reflux for 11 hours. The solution was concentrated to leave a yellow solid, which was basified with saturated potassium carbonate solution and washed with chloroform (3×60 ml). The aqueous solution was acidified with 11M hydrochloric acid and concentrated in vacuo to leave a yellow solid, which was heated under reflux in methanolic hydrogen chloride (140 ml) for 1.5h. The mixture was filtered and the filtrate concentrated to leave a yellow oil, which was treated with saturated potassium carbonate solution and extracted with chloroform (3×70 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give an orange oil, which was purified by column chromatography on silica gel eluting with 10% methanol/chloroform to give a yellow oil (2.50 g). This was converted into the oxalate salt and recrystallised from methanol/ether to give the title compound (E3) as a white solid m.p. 114°-116° C.

Workup

  1. filtrationThe catalyst was filtered off through kieselguhr
  2. concentrationthe filtrate concentrated in vacuo
  3. customto leave a yellow semi-solid, which
  4. temperatureheated
  5. temperatureunder reflux for 11 hours
  6. concentrationThe solution was concentrated
  7. customto leave a yellow solid, which
  8. washwashed with chloroform (3×60 ml)
  9. concentrationconcentrated in vacuo
  10. customto leave a yellow solid, which
  11. temperaturewas heated
  12. filtrationThe mixture was filtered
  13. concentrationthe filtrate concentrated
  14. customto leave a yellow oil, which
  15. extractionextracted with chloroform (3×70 ml)
  16. dry with materialThe combined extracts were dried (Na2SO4)
  17. concentrationconcentrated in vacuo
  18. customto give an orange oil, which
  19. customwas purified by column chromatography on silica gel eluting with 10% methanol/chloroform

Sources & evidence

ORD record
ord-7584cde3d7d34791b646db6e25be35af
Source dataset
uspto-grants-1992_07
Patent number
US05132316

Reaction notes

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