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 595816Notes

Reaction equation

HRID 595816 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-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To tert-butyl 3-(6-aminopyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (180 mg, 0.482 mmol) in MeOH (10 mL) under N2 atmosphere was added Pd—C (103 mg, 0.096 mmol). The reaction mixture was stirred at room temperature under H2 balloon. After 2 h, the reaction mixture was filtered through Celite pad, washed with methanol and evaporated to provide desired product, which proceeded for next step without purification (150 mg, 71%). LCMS (m/z): 264.2 (MH+), 0.565 min.

Workup

  1. filtrationthe reaction mixture was filtered through Celite pad
  2. washwashed with methanol
  3. customevaporated

Sources & evidence

ORD record
ord-ce4937b0dea5404b8987b5f395f5e7de
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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