Potassium Carbonate → Tert-butyl 6-(pyrrolidin-1-ylmethyl)pyridin-2-ylcarbamate

HRID 2359450Notes

Reaction equation

HRID 2359450 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:8]=1)(=O)=O.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>C(#N)C>[N:21]1([CH2:6][C:7]2[N:8]=[C:9]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[CH:11][CH:12]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 19349110(6-(Tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate

Product 1

HCID 66694553Tert-butyl 6-(pyrrolidin-1-ylmethyl)pyridin-2-ylcarbamateYield 84.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing (6-(tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate (1.30 g, 3.2 mmol), pyrrolidine (0.46 g, 6.4 mmol) and K2CO3 (1.30 g, 9.6 mmol) in acetonitrile (15 mL) was stirred at room temperature for 12 h. Saturated aqueous NaHCO3 was added and the mixture was concentrated under reduced pressure. The resulting aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford tert-butyl 6-(pyrrolidin-1-ylmethyl)pyridin-2-ylcarbamate (0.75 g, 2.7 mmol, 62% for two steps).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionThe resulting aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-327108a70a9b4be19bce956a2b603a70
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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