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 729446Notes

Reaction equation

HRID 729446 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]2[CH2:14][N:15](CC3C=CC=CC=3)[CH2:16][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]2[CH2:14][NH:15][CH2:16][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 21041208tert-butyl 2-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 19691292tert-Butyl octahydro-5H-pyrrolo(3,4-c)pyridine-5-carboxylateYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Benzyloctahydropyrrolo[3,4-c]pyridine-5-carboxylic acid tert-butyl ester (Example A26, 24.98 g, 78.8 mmol) in 400 mL of methanol is treated with 2.5 g of 20% Pd/C and shaken for 20.5 hours under 50 PSI of hydrogen. The solution is filtered and concentrated to afford 17.8 g of the title compound as a solid. MS APCI: m/z 228 (MH+).

Workup

  1. filtrationThe solution is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f44e53249df54f26ab25a19c9ac68829
Source dataset
uspto-grants-2009_09
Patent number
US07582627B2

Reaction notes

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