Hydrazinium chloride → HCID 178451527, compound

HRID 2264307Notes

Reaction equation

HRID 2264307 reaction equation
[C:1]([CH:3]1[C:7](=O)[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2].Cl.[NH2:17][NH2:18].C(=O)([O-])O.[Na+]>C(O)C>[NH2:2][C:1]1[NH:18][N:17]=[C:7]2[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][C:3]=12

Participants

5

Reactant 3

HCID 115031Hydrazinium chlorideHCID 516892Sodium BicarbonateHCID 2756790tert-Butyl 3-cyano-4-oxopyrrolidine-1-carboxylate

Product 1

HCID 178451527HCID 178451527, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1 g (4.76 mmol) of tert-butyl 3-cyano-4-oxopyrrolidine-1 carboxylate in ethanol (28 mL) was added 0.326 g (4.76 mmol) of hydrazine hydrochloride and the reaction mixture heated at ° C. for 3 h. The mixture was cooled to 0° C. and saturated aqueous sodium hydrogen carbonate (60 mL) added. The solvent was evaporated in vacuo and the aqueous phase extracted with ethyl acetate (10×10 mL). The combined organic fractions were dried (anhydrous sodium sulfate), filtered and the solvent evaporated in vacuo. The resulting residue was chromatographed on a Biotage Horizon® system (silica gel, 0 to 10% methanol/ethyl acetate gradient) to yield the title compound as a orange solid. LC/MS 225.2 (M+1).

Workup

  1. temperaturethe reaction mixture heated at ° C
  2. customThe solvent was evaporated in vacuo
  3. extractionthe aqueous phase extracted with ethyl acetate (10×10 mL)
  4. dry with materialThe combined organic fractions were dried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe resulting residue was chromatographed on a Biotage Horizon® system (silica gel, 0 to 10% methanol/ethyl acetate gradient)

Sources & evidence

ORD record
ord-e84d2257fb244c1580ba909c5185f7e4
Source dataset
uspto-grants-2010_12
Patent number
US07855206B2

Reaction notes

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