Potassium Carbonate → HCID 67280827, compound

HRID 1671617Notes

Reaction equation

HRID 1671617 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]2[CH:19]([OH:20])[CH2:18][NH:17][CH2:16]2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:22]([O-:25])([O-])=[O:23].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:15]2[CH:19]([OH:20])[CH2:18][N:17]([CH2:13][CH2:8][NH:7][C:22]([O:25][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:23])[CH2:16]2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 598580021,1-Dimethylethyl N-[6-[(4-hydroxy-3-pyrrolidinyl)methyl]-2-pyridinyl]carbamate

Product 1

HCID 67280827HCID 67280827, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [6-(4-hydroxy-pyrrolidin-3-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester II-1 (0.01 mol), (2-bromo-ethyl)-carbamic acid tert-butyl (0.012 mol), anhydrous K2CO3 (0.02 mol) in 50 mL anhydrous DMF was stirred at room temperature overnight. Solids were filtered off. The filtrate was evaporated under reduced pressure. The residue was partitioned between EtOAc and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, and evaporated in vacuo. The obtained residue was purified by column chromatography (silica gel, CH2Cl2:MeOH, 9:1). (57%)

Workup

  1. filtrationSolids were filtered off
  2. customThe filtrate was evaporated under reduced pressure
  3. customThe residue was partitioned between EtOAc and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated in vacuo
  7. customThe obtained residue was purified by column chromatography (silica gel, CH2Cl2:MeOH, 9:1)

Sources & evidence

ORD record
ord-c3aa29300dc34e698486f713ac01297f
Source dataset
uspto-grants-2011_08
Patent number
US07994326B2

Reaction notes

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