Hydrogen Bromide → HCID 14810910, compound

HRID 2257421Notes

Reaction equation

HRID 2257421 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]2[CH2:13][CH2:14][O:15][C:16](=[O:17])[C@H:10]2[CH2:9]1)[C:2]1C=CC=CC=1.Br.C(=O)([O-])[O-].[K+].[K+].C(=O)=O>C(O)C.C(Cl)(Cl)Cl>[CH2:14]([O:15][C:16]([CH:10]1[CH:11]2[CH2:12][N:8]([CH2:1][CH2:2]2)[CH2:9]1)=[O:17])[CH3:13]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 14955036HCID 14955036, compound

Product 1

HCID 14810910HCID 14810910, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

(±) cis-2-benzyl-hexahydropyrano[3,4-c]pyrrole-4(1H)-one (D20) (180 g, 0.78 mole) in ethanol (400 ml) was stirred and cooled to 0° C. and hydrogen bromide gas introduced at such a rate that the temperature did not rise above 20° C. until the solution was saturated. The reaction was allowed to stand at room temperature for 6 h. The reaction was then poured into a well stirred mixture of chloroform (2 L) and saturated aqueous potassium carbonate solution (1.5 L) which was cooled by the addition of solid carbon dioxide. The organic layer was separated and the aqueous layer extracted with chloroform (4×1 L). The combined organic extracts were dried (Na2SO4) concentrated in vacuo to a gum. The gum was then stirred with ether (3×750ml) to remove any unreacted starting material and the ether insoluble gum dissolved in ethanol (1 L). Palladium on charcoal 10% (20 g) was then added and the mixture stirred under an atmosphere of hydrogen at 50° C. for 6 h when the uptake of hydrogen was complete. The reaction was then filtered through Kieselguhr and concentrated in vacuo to a gum. This was partitioned between chloroform and saturated aqueous potassium carbonate solution. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo to a gum. Distillation in vacuo afforded the title compound (D21, 75 g, 0.44 mole, 56%) as an oil b.p. 90°-95° C.0.5mmHg

Workup

  1. customdid not rise above 20° C. until the solution
  2. additionThe reaction was then poured into a well
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with chloroform (4×1 L)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo to a gum
  7. stirringThe gum was then stirred with ether (3×750ml)
  8. customto remove
  9. dissolutionthe ether insoluble gum dissolved in ethanol (1 L)
  10. additionPalladium on charcoal 10% (20 g) was then added
  11. stirringthe mixture stirred under an atmosphere of hydrogen at 50° C. for 6 h when the uptake of hydrogen
  12. filtrationThe reaction was then filtered through Kieselguhr
  13. concentrationconcentrated in vacuo to a gum
  14. customThis was partitioned between chloroform and saturated aqueous potassium carbonate solution
  15. customThe organic phase was separated
  16. dry with materialdried over sodium sulphate
  17. concentrationconcentrated in vacuo to a gum
  18. distillationDistillation in vacuo

Sources & evidence

ORD record
ord-5e6116f0d76948b8bb75351b17fcac47
Source dataset
uspto-grants-1997_08
Patent number
USRE035593

Reaction notes

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