Ethyl Acetate → (+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile

HRID 1295069Notes

Reaction equation

HRID 1295069 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]([NH2:13])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C>C1COCC1>[CH3:1][C:2]1([CH3:14])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]#[N:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 178421816HCID 178421816, compound

Product 1

HCID 178421815(+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(±)-1,1-Dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid amide (0.532 g, 2.79 mmol) was taken up in THF (150 mL) and trifluoroacetic anhydride (0.936 g, 4.46 mmol) added. The resulting solution was stirred at room temperature under argon for 1 hour. Ethyl acetate (50 mL) was added and solvent removed under reduced pressure. The resulting pale yellow oil was taken up in DCM (100 mL), washed with saturated aqueous sodium bicarbonate solution (40 mL) and solvent removed under reduced pressure. The resulting white solid was taken up as a suspension in DCM (20 mL) and filtered to give (±)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile as an off-white solid. m/z (ES): 174 [M+H]+

Workup

  1. customsolvent removed under reduced pressure
  2. washwashed with saturated aqueous sodium bicarbonate solution (40 mL) and solvent
  3. customremoved under reduced pressure
  4. filtrationfiltered

Sources & evidence

ORD record
ord-d0c8b36b36ee4018a8bd67a11aee76d4
Source dataset
uspto-grants-2007_07
Patent number
US07241792B2

Reaction notes

Loading…