tert-butyl 5-benzyloctahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate → (3aR,7aS)-rel-tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

HRID 2066485Notes

Reaction equation

HRID 2066485 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH:11]([CH2:12][N:13](CC3C=CC=CC=3)[CH2:14][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH:11]([CH2:12][NH:13][CH2:14][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 58117138tert-butyl 5-benzyloctahydro-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 99%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

To a solution of (5-benzyl-octahydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (777 mg, 2.46 mmol) in IMS (20 mL) was added palladium hydroxide on carbon (5%, 50 mg) and the mixture stirred under a hydrogen atmosphere at RT for 10 h. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give the title compound as a straw coloured oil (550 mg, 99%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-7c36c9f415994bfba9a3453048c20144
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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