(4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate → (4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

HRID 1667112Notes

Reaction equation

HRID 1667112 reaction equation
C([N:8]1[CH2:16][C@H:15]2[C@H:10]([N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:13][CH2:14]2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:13][CH2:14][C@H:15]2[CH2:16][NH:8][CH2:9][C@@H:10]12

Participants

4

Reactant 1

HCID 29973012(4aS,7aS)-tert-butyl 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

Product 1

HCID 1519435(4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The product from Example 50A (0.15 g, 0.5 mmol) in methanol (80 mL) was hydrogenated (4 pounds per square inch) in the presence of palladium hydroxide on carbon (0.42 g) for 3 hours at room temperature. The reaction mixture was filtered and concentrated to yield the title compound. MS (DCI) m/z 227 (M+H)+.

Workup

  1. customfor 3 hours
  2. customat room temperature
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-362870eaaf9c4d0dbb32ddfa06744e6a
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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