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

HRID 520483Notes

Reaction equation

HRID 520483 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 84.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (6-(tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate 79 (1.30 g, 3.2 mmol), pyrrolidine 68 (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 80 (0.75 g, 62% yield).

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-cd60a7e88b1b4db19c874efd1d53601b
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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