Potassium Carbonate → (S)-tert-butyl 2-(5-ethynyl-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 1919179Notes

Reaction equation

HRID 1919179 reaction equation
C([O-])([O-])=O.[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[NH:17][C:16]([C@@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[N:15][CH:14]=1)(C)C>CO>[C:12]([C:13]1[NH:17][C:16]([C@@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[N:15][CH:14]=1)#[CH:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58498689(S)-tert-butyl 2-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 58498809(S)-tert-butyl 2-(5-ethynyl-1H-imidazol-2-yl)pyrrolidine-1-carboxylateYield 49.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

K2CO3 (118 mg, 0.855 mmol) was added to a solution of (S)-tert-butyl 2-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (950 mg, 2.85 mmol) in MeOH (25 mL) and the reaction mixture was stirred at RT for 1 h and then heated at 25° C. for 3 h. The reaction was concentrated to remove the volatiles and the residue was taken into MeOH and filtered through a Strata XC MCX cartridge. The cartridge was washed with methanol and the compound was release from the cartridge by eluting with a solution of 2M of ammonia/methanol (40 mL) and concentrated to give a (S)-tert-butyl 2-(5-ethynyl-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (530 mg, 1.41 mmol, 49.6% yield).

Workup

  1. temperatureheated at 25° C. for 3 h
  2. concentrationThe reaction was concentrated
  3. customto remove the volatiles
  4. filtrationfiltered through a Strata XC MCX cartridge
  5. washThe cartridge was washed with methanol
  6. washby eluting with a solution of 2M of ammonia/methanol (40 mL)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-072e82080eca4d7a96247fad98cc0879
Source dataset
uspto-grants-2013_12
Patent number
US08618153B2

Reaction notes

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