Trifluoroacetic acid → [4-Tert-butyl-2-(piperidin-1-ylmethyl)phenoxy]acetic acid

HRID 1350857Notes

Reaction equation

HRID 1350857 reaction equation
[C:1]([C:5]1[CH:19]=[CH:18][C:8]([O:9][CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])=[C:7]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([C:5]1[CH:19]=[CH:18][C:8]([O:9][CH2:10][C:11]([OH:13])=[O:12])=[C:7]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 58640406Tert-butyl [4-tert-butyl-2-(piperidin-1-ylmethyl)phenoxy]acetate

Product 1

HCID 21097492[4-Tert-butyl-2-(piperidin-1-ylmethyl)phenoxy]acetic acidYield 173.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene dichloride (2.0 ml) solution of tert-butyl [4-tert-butyl-2-(piperidin-1-ylmethyl)phenoxy]acetate (75 mg, 0.21 mmol), trifluoroacetic acid (0.2 ml, 2.7 mmol) was added at ambient temperature under nitrogen atmosphere. After being stirred for 15 hours, additional trifluoroacetic acid (1.0 ml, 13.5 mmol) was added. After being stirred additionally for 10 hours, the resulting mixture was concentrated under reduced pressure and azeotrope with toluene to furnish 111 mg of the title compound as slightly yellow oil, which was used for the next reaction without further purification.

Workup

  1. stirringAfter being stirred additionally for 10 hours
  2. concentrationthe resulting mixture was concentrated under reduced pressure and azeotrope with toluene

Sources & evidence

ORD record
ord-6748d12edc8c4f65a61ee22ad9a9716b
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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