Trifluoroacetic acid → 1-Benzyl-4-(4,5-dibromo-thiophen-2-yl)-pyrrolidine-3-carboxylic acid trifluoroacetate

HRID 1013360Notes

Reaction equation

HRID 1013360 reaction equation
C([O:5][C:6]([CH:8]1[CH:12]([C:13]2[S:14][C:15]([Br:19])=[C:16]([Br:18])[CH:17]=2)[CH2:11][N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9]1)=[O:7])(C)(C)C.[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30]>C(Cl)Cl>[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[CH2:20]([N:10]1[CH2:11][CH:12]([C:13]2[S:14][C:15]([Br:19])=[C:16]([Br:18])[CH:17]=2)[CH:8]([C:6]([OH:7])=[O:5])[CH2:9]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 672073381,1-Dimethylethyl 4-(4,5-dibromo-2-thienyl)-1-(phenylmethyl)-3-pyrrolidinecarboxylate

Product 1

HCID 672062341-Benzyl-4-(4,5-dibromo-thiophen-2-yl)-pyrrolidine-3-carboxylic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step b) (2.6 g, 5.2 mmol) in CH2Cl2 (25 ml) and trifluoroacetic acid (TFA) (75 ml) was stirred at 22° C. for 16 hours. Next, the solvent was evaporated and toluene (50 ml) was added and subsequently evaporated in vacuo at 40° C. to remove residual TFA. The crude subtitle product was used without further purification.

Workup

  1. customNext, the solvent was evaporated
  2. additiontoluene (50 ml) was added
  3. customsubsequently evaporated in vacuo at 40° C.
  4. customto remove residual TFA
  5. customThe crude subtitle product was used without further purification

Sources & evidence

ORD record
ord-55593deda0394cd2a40c0c3643d35556
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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