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

HRID 85151Notes

Reaction equation

HRID 85151 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 (94; 1.30 g, 3.2 mmol), pyrrolidine (95; 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 96 (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-afa723715b61454d84674eecb3ea7d75
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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