Potassium Carbonate → HCID 178435838, compound

HRID 1625514Notes

Reaction equation

HRID 1625514 reaction equation
[CH3:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]2[NH:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[C:26][Si](C)(C)C)=[CH:21][CH:20]=3)[N:18]=2)[CH2:3]1.C([O-])([O-])=O.[K+].[K+]>CO>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([C:17]2[N:18]=[C:14]([C@@H:4]3[CH2:3][C@H:2]([CH3:1])[CH2:6][N:5]3[C:7]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:8])[NH:15][CH:16]=2)=[CH:24][CH:23]=1)#[CH:26]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178461452tert-butyl (2S,4S)-4-methyl-2-[4-[4-(2-trimethylsilylethynyl)phenyl]-1H-imidazol-2-yl]pyrrolidine-1-carboxylate

Product 1

HCID 178435838HCID 178435838, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (2S,4S)-4-methyl-2-[4-[4-(2-trimethylsilylethynyl)phenyl]-1H-imidazol-2-yl]pyrrolidine-1-carboxylate (57 mg, 0.1346 mmol) in MeOH (2 mL) is added K2CO3 (37.2 mg, 0.27 mmol). The mixture is stirred at rt for 2 hours. After removal of the solvent under reduced pressure, the residue is purified by flash column chromatography on silica gel using 0-5% MeOH/CH2Cl2 to provide tert-butyl (2S,4S)-2-[4-(4-ethynylphenyl)-1H-imidazol-2-yl]-4-methyl-pyrrolidine-1-carboxylate (47 mg, 99%).

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. customthe residue is purified by flash column chromatography on silica gel using 0-5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-6ab6e1c58d6e4ba792da97a7e12dc94c
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

Loading…