1-Tert-butyloxycarbonyl-trans-3-benzyloxycarbonylamino-4-(2-pyridyl)pyrrolidine → 1-Tert-butyloxycarbonyl-trans-3-amino-4-(2-pyridyl)pyrrolidine

HRID 398400Notes

Reaction equation

HRID 398400 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([NH:19]C(OCC2C=CC=CC=2)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([NH2:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 700235531-Tert-butyloxycarbonyl-trans-3-benzyloxycarbonylamino-4-(2-pyridyl)pyrrolidine

Product 1

HCID 590855601-Tert-butyloxycarbonyl-trans-3-amino-4-(2-pyridyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-tert-butyloxycarbonyl-trans-3-benzyloxycarbonylamino-4-(2-pyridyl)pyrrolidine from step 6 above (3.9 g, 9.8 mmol) in EtOH (25 mL) was added 10% Pd on carbon (1.5 g). The mixture was shaken under an atmosphere of hydrogen (40 psi) at ambient temperature for 18 h on a Parr apparatus. The catalyst was removed by filtration and the solvent was removed in vacuo to give the title compound as an oil (2.5 g, HPLC RT=3.96 min, method A).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-06962b7c9eac451094bdd14a5fecf5f0
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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