Tetrahydrofuran → (S)-3-(5-amino-pyridin-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl ester

HRID 1645341Notes

Reaction equation

HRID 1645341 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][N:13]=2)[CH2:7]1)=[O:5])[CH3:2].C1COCC1>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][N:13]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 66773521HCID 66773521, compound

Product 1

HCID 59365133(S)-3-(5-amino-pyridin-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The above (S)-3-(5-nitropyridine-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl ester (2.59 g, 9.25 mmol) was suspended in ethanol (50 mL) and THF (10 mL) was added. The mixture was gently heated to give a clear solution and 10% palladium on carbon (250 mg) was added. The mixture was hydrogenated at 45 psi for 4 hrs and then filtered. The filtrate was concentrated to give a purple solid as (S)-3-(5-amino-pyridin-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl ester (2.3 g, 100% yield). LCMS for C12H18N4O2 calcd (m/e) 250, obsd 251 (M+H).

Workup

  1. temperatureThe mixture was gently heated
  2. additionwas added
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8856e87994864932a46e12ed40928372
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

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