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

HRID 921809ノート

反応式

HRID 921809 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ad4edb30b7a04a4da8be1014c64affbd
出典データセット
uspto-grants-2016_03
特許番号
US09273057B2

反応ノート

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