Trifluoroacetic acid → HCID 118590492, compound

HRID 1054441Notes

Reaction equation

HRID 1054441 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1(O)[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118590599HCID 118590599, compound

Product 1

HCID 118590492HCID 118590492, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stifled solution of tert-butyl 2-(2,5-difluorophenyl)-2-hydroxypiperidine-1-carboxylate (9.4 g, 30 mmol) in DCM was added TFA (34.2 g, 300 mmol) and stifled at room temperature for 2 h. After completion of reaction, solvent was removed under vacuum and residue was quenched with sat.NaHCO3 and extracted with DCM. Organic layer was washed with water, brine and dried over anhydrous Na2SO4 and concentration to afford crude product as brown liquid (5.5 g), this crude was directly used for next step without any purification.

Workup

  1. customAfter completion of reaction, solvent
  2. customwas removed under vacuum and residue
  3. customwas quenched
  4. extractionNaHCO3 and extracted with DCM
  5. washOrganic layer was washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4 and concentration

Sources & evidence

ORD record
ord-3a9707667a164df3a3d3f4676d74599b
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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