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 1431106Notes

Reaction equation

HRID 1431106 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]=[C:10]([C:13]2[CH:14]=[N:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:19][C:16]1[N:15]=[CH:14][C:13]([CH:10]2[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]2)=[CH:18][CH:17]=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 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

3-(6-Amino-pyridin-3-yl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (538 mg, 2.06 mmol, Eq: 1.00) was dissolved in methanol (20 ml). The solution was put under argon and then treated with palladium on activated carbon (43.8 mg, 20.6 μmol, Eq: 0.01). The suspension was purged with hydrogen and stirred under hydrogen for 18 h. The reaction mixture was filtered through silica gel. The filtrate was concentrated and the residue was dissolved in methanol (12 ml). The solution was purged with argon for 10 min and then treated with palladium on activated carbon (Degussa) (43.8 mg, 20.6 μmol, Eq: 0.01). The suspension was purged with hydrogen and stirred under hydrogen for 18 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 (422 mg, 78%). LC/MS-ESI observed [M+H]+ 264.

Workup

  1. customThe suspension was purged with hydrogen
  2. filtrationThe reaction mixture was filtered through silica gel
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in methanol (12 ml)
  5. customThe solution was purged with argon for 10 min
  6. customThe suspension was purged with hydrogen
  7. stirringstirred under hydrogen for 18 h
  8. filtrationThe reaction mixture was filtered through a 45 μm frit
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bd2b318376e94b87957d4b2952991d15
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

Loading…