Trifluoroacetic acid → (S)-5-((3,4-Dimethoxyphenoxy)methyl)-1-methyl-3-(pyrrolidin-2-yl)-1H-pyrazole

HRID 710052Notes

Reaction equation

HRID 710052 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:6][CH2:7][C:8]1[N:12]([CH3:13])[N:11]=[C:10]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2C(OC(C)(C)C)=O)[CH:9]=1.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:6][CH2:7][C:8]1[N:12]([CH3:13])[N:11]=[C:10]([C@@H:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)[CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86706764(S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86706765(S)-5-((3,4-Dimethoxyphenoxy)methyl)-1-methyl-3-(pyrrolidin-2-yl)-1H-pyrazoleYield 102%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a CHCl3 (1.0 mL) solution of the compound (365 mg) obtained in Example 13-(2), TFA (5.0 mL) was added at 0° C. and the mixture was stirred at room temperature for 2 hours. After concentrating the reaction mixture, saturated aqueous sodium bicarbonate (50 mL) was added and the organic layer extracted with CHCl3 (50 mL×2) was dried (Na2SO4), filtered and concentrated to give the titled compound (283 mg, pale brown oil.)

Workup

  1. concentrationAfter concentrating the reaction mixture, saturated aqueous sodium bicarbonate (50 mL)
  2. additionwas added
  3. extractionthe organic layer extracted with CHCl3 (50 mL×2)
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c2f5bbf9c3234ffd97451368cc61d6e9
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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