tert-butyl 2-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate → tert-Butyl octahydro-5H-pyrrolo(3,4-c)pyridine-5-carboxylate

HRID 712468Notes

Reaction equation

HRID 712468 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([CH2:11][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:14]2)[CH2:9]1)C1C=CC=CC=1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH2:16]1[CH:15]2[CH:10]([CH2:11][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:14]2)[CH2:9][NH:8]1

Participants

4

Reactant 1

HCID 21041208tert-butyl 2-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate

Product 1

HCID 19691292tert-Butyl octahydro-5H-pyrrolo(3,4-c)pyridine-5-carboxylateYield 60%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate (1.60 g) in EtOAc was added a catalytic amount of 20% Pd(OH)2/C. The suspension was stirred for 3 h at room temperature under H2 and filtered. The filtrate was concentrated in vacuo to give the title compound as colorless oil (0.68 g, 60%). The crude product was used for the next step without further purification. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 227.4 (M+1).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2824c8459aa04b42af0382bddeba3712
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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