Triethylamine → HCID 22120931, compound

HRID 1274238Notes

Reaction equation

HRID 1274238 reaction equation
FC(F)(F)S(O[C:7]1[CH:14]2[CH2:15][N:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9][CH:8]=1)(=O)=O.[CH2:18](N(CC)CC)C.[C]=O.[C:27]([O-:30])([O-])=[O:28].[K+].[K+]>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:10]12[CH2:15][CH:14]([CH2:13][CH2:12][CH2:11]1)[C:7]([C:27]([O:30][CH3:18])=[O:28])=[CH:8][CH2:9]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 22120938HCID 22120938, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 22120931HCID 22120931, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A stirred solution of 4-trifluoromethanesulphonyloxy-1-azabicyclo[3.3.1]non-3-ene (D6, 2.5 g, ≤0.0092 mole) in methanol (15 ml) was treated with triethylamine (2.6 ml, 0.018 mole) and triphenylphosphine (135 mg, 0.52 mmole), then carbon monoxide was bubbled through the stirring solution for 5 minutes, before palladium (II) acetate (60 mg, 0.27 mmole) was added. The reaction flask was sealed under a carbon monoxide balloon and stirred at 25° C. for 20 h. The mixture was filtered through a pad of kieselguhr and the filtrate was concentrated in vacuo. The residue was treated with 2M HCl acid (30 ml) and ethyl acetate (30 ml), then shaken well and the acid layer isolated, basified with solid K2CO3 and extracted with chloroform. The extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow oil (0.99 g, 54%).

Workup

  1. additionwas added
  2. customThe reaction flask was sealed under a carbon monoxide balloon
  3. filtrationThe mixture was filtered through a pad of kieselguhr
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionThe residue was treated with 2M HCl acid (30 ml) and ethyl acetate (30 ml)
  6. stirringshaken well
  7. customthe acid layer isolated
  8. extractionextracted with chloroform
  9. dry with materialThe extract was dried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f0cb7fb137d40feba288994cca0699f
Source dataset
uspto-grants-2000_12
Patent number
US06156783

Reaction notes

Loading…