Carbon Dioxide → HCID 19610921, compound

HRID 1602334Notes

Reaction equation

HRID 1602334 reaction equation
[C:1](O)(=O)[C:2](O)=O.[N:7]([CH:10]1[CH:15]2[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]2)[CH2:11]1)=[N+:8]=[N-:9].C(C(O)=O)#CC(O)=O.C1(C)C(C)=CC=CC=1.C(=O)=O>CC(C)=O>[N:7]1([CH:10]2[CH:15]3[CH2:14][CH2:13][N:12]([CH2:17][CH2:16]3)[CH2:11]2)[CH:2]=[CH:1][N:9]=[N:8]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 3712-Butynedioic acidHCID 7237O-XyleneHCID 19610894HCID 19610894, compound

Product 1

HCID 19610921HCID 19610921, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(±) 3-Azido-1-azabicyclo[2.2.2]octane oxalate salt (D25) (200 mg, 0.0083 mole) in acetone (20 ml) was treated with acetylene dicarboxylic acid (500 mg, 0.0044 mole) and concentrated in vacuo to produce a homogenous gum. Xylene (20 ml) was added and the solution heated to reflux for 10 min when the suspension rapidly darkened and evolved carbon dioxide. The xylene was then removed in vacuo and the residue 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. Chromatography on alumina in a gradient of 5-30% methanol in ethyl acetate afforded the title compound (E35) which crystallised from 40-60° petrol as needles m.p. 62-65° C. (60 mg, 0.0034 moles, 40%).

Workup

  1. concentrationconcentrated in vacuo
  2. customto produce a homogenous gum
  3. temperaturethe solution heated
  4. temperatureto reflux for 10 min when the suspension
  5. customThe xylene was then removed in vacuo
  6. customthe residue partitioned between chloroform and saturated aqueous potassium carbonate solution
  7. customThe organic phase was separated
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated in vacuo to a gum

Sources & evidence

ORD record
ord-0a42ef613d474c348e775e7f7740b24f
Source dataset
uspto-grants-1999_11
Patent number
US05981545

Reaction notes

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