tert-butyl 3-(6-aminopyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate → Tert-butyl 3-(6-aminopyridin-3-yl)pyrrolidine-1-carboxylate

HRID 449630Notes

Reaction equation

HRID 449630 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=2)=[CH:4][CH:3]=1>CO.[Pd]>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66742367tert-butyl 3-(6-aminopyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 66742238Tert-butyl 3-(6-aminopyridin-3-yl)pyrrolidine-1-carboxylateYield 107.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 3-(6-aminopyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (1.5 g, 5.74 mmol, Eq: 1.00) was dissolved in MeOH (60 ml). The solution was purged with argon and then treated with palladium on activated carbon (Degussa) (6.11 mg, 57.4 μmol, Eq: 0.01). The suspension was purged with hydrogen and stirred under a hydrogen atmosphere for 48 h. The reaction mixture was filtered through a 45 μm frit. The filtrate was concentrated in vacuo to give tert-butyl 3-(6-aminopyridin-3-yl)pyrrolidine-1-carboxylate (1.63 g) The enantiomers were separated using chiral SFC HPLC.

Workup

  1. customThe solution was purged with argon
  2. customThe suspension was purged with hydrogen
  3. filtrationThe reaction mixture was filtered through a 45 μm frit
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-70ed3c7ce472402aa8d1a228120aa090
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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