Trifluoroacetic acid → HCID 67326759, compound

HRID 1465998Notes

Reaction equation

HRID 1465998 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]3[CH2:20][CH2:19][NH:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71009683HCID 71009683, compound

Product 1

HCID 67326759HCID 67326759, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.55 g (4.17 mmol) of tert-butyl 3-(4′-fluorobiphenyl-4-yloxymethyl)pyrrolidine-1-carboxylate are dissolved in 40 ml of dichloromethane and then, at 0° C., 6.00 ml (80.77 mmol) of trifluoroacetic acid are subsequently added. After stirring at ambient temperature for two hours, the mixture is concentrated to dryness and then the residue is taken up in water and dichloromethane. A saturated sodium hydrogencarbonate solution is added and then the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with a saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated under vacuum. 0.98 g of product is obtained in the form of an oil, used as is in the following stage.

Workup

  1. concentrationthe mixture is concentrated to dryness
  2. additionA saturated sodium hydrogencarbonate solution is added
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. washThe combined organic phases are washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2228172db5484c3e9b149137d17c7fd5
Source dataset
uspto-grants-2015_04
Patent number
US09000010B2

Reaction notes

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