Hydrazine → HCID 69336447, compound

HRID 1295358Notes

Reaction equation

HRID 1295358 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)([CH2:11]2)[CH:9]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NN>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([CH2:14][NH2:15])([CH2:11]2)[CH:9]1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 693429221-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester2×

Product 1

HCID 69336447HCID 69336447, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the starting material, 1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (0.560 g, 1.34 mmol) (Intermediate 20) was added ethanol (10 mL) and hydrazine (35% in H2O, 0.483 mL, 5.36 mmol). The reaction was heated to reflux, and although within a few minutes a solid precipitated that impeded stirring, the reaction was heated for a total of 80 minutes. The solvent was removed at reduced pressure and the residue partitioned between 1N NaOH solution and methylene chloride. The organics were washed with a saturated solution of citric acid two times and the methylene chloride discarded. The aqueous layer was basified with sodium bicarbonate and extracted with methylene chloride. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to give 1-aminomethyl-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester as an oil (0.268 g, 69% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customalthough within a few minutes a solid precipitated that
  4. temperaturethe reaction was heated for a total of 80 minutes
  5. customThe solvent was removed at reduced pressure
  6. customthe residue partitioned between 1N NaOH solution and methylene chloride
  7. washThe organics were washed with a saturated solution of citric acid two times
  8. extractionextracted with methylene chloride
  9. washThe organics were washed with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-7a18744dd9ea4ad08fdc39a92acd3af4
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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