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

HRID 712429Notes

Reaction equation

HRID 712429 reaction equation
[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.COCCO>[OH-].[OH-].[Pd+2].CC(O)=O>[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

Participants

5

Reactant 2

HCID 80192-MethoxyethanolHCID 20042876tert-Butyl 1H-pyrrolo(3,2-c)pyridine-1-carboxylate

Product 1

HCID 49761056(3aR,7aS)-rel-tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.55 g) in the mixture solvent of glycol monomethyl ether (40 mL) and AcOH (1 mL) was added a catalytic amount of Pd(OH)2/C. The suspension was heated at 70° C. for 24 h under H2 (2.0 MPa) and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the product as viscous liquid (2.64 g, 100.00%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-6120a2c00b7c446390f749605507b971
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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