Acetic Acid → (3aR,7aS)-rel-tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

HRID 921809노트

반응식

HRID 921809 반응식
[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.C(O)(=O)C>C(O)C.[OH-].[OH-].[Pd+2]>[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:9]2[CH:4]([CH2:5][NH:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 20042876tert-Butyl 1H-pyrrolo(3,2-c)pyridine-1-carboxylate

생성물 1

HCID 49761056(3aR,7aS)-rel-tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate수율 74.6%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

A mixture of tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.45 g, 11.23 mmol) and palladium hydroxide on carbon (20%, 1 g, 1.424 mmol) in ethanol (8 ml)/acetic acid (16 mL) was hydrogenated at 50 psi and 60° C. overnight. The reaction mixture was filtered through celite. Solvent was evaporated in vacuo and the residue was diluted with dichloromethane and washed with saturated sodium bicarbonate. The aqueous layer was extracted with dichloromethane two more times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo, The crude was be used without purification. tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1.896 g) was obtained as a colorless oil.

후처리

  1. customwas hydrogenated at 50 psi and 60° C. overnight
  2. filtrationThe reaction mixture was filtered through celite
  3. customSolvent was evaporated in vacuo
  4. additionthe residue was diluted with dichloromethane
  5. washwashed with saturated sodium bicarbonate
  6. extractionThe aqueous layer was extracted with dichloromethane two more times
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude was be used without purification

출처 및 근거

ORD 기록
ord-ad4edb30b7a04a4da8be1014c64affbd
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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