Hydrazine → HCID 69336447, 화합물

HRID 1295358노트

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HRID 1295358 반응식
[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]

참가 물질

4

반응물 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 ester2회

생성물 1

HCID 69336447HCID 69336447, 화합물수율 69.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7a18744dd9ea4ad08fdc39a92acd3af4
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241798B2

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