Phenol → Trifluoroacetic acid
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:18]=[CH:17][O:16][C:15]=2[CH2:19][O:20]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][CH2:9]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].[C:37]1(O)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>CC#N>[O:20]([CH2:19][C:15]1[O:16][CH:17]=[CH:18][C:14]=1[CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]Participants
Reactant 4
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
4-[2-(Toluene-4-sulfonyloxymethyl)furan-3-yl]piperidine-1-carboxylic acid t-butyl ester (65 mg, 0.15 mmol, 1.0 eq.) was dissolved in MeCN (770 μL) and added to a mixture of potassium carbonate (32 mg, 230 mmol, 1.6 eq.) and phenol (21.1 mg, 224 μmol, 1.5 eq.). The resulting mixture was shaken at 50° C. overnight. The mixture was then cooled and the solids removed. The supernatant was combined with TFA (12 μL, 160 mmol, 1.0 eq.) and the resulting mixture was shaken overnight at room temperature. The solution was concentrated using an evaporator, then dissolved in 1:1 AcOH:H2O (5.0 mL) then an additional 2.0 ml AcOH, filtered, and purified by preparative HPLC to yield the title compound as a TFA salt (1.4 mg, 88% purity). MS m/z: [M+H]+ calcd for C16H19NO2, 258.14. found 258.2.
Workup
- temperatureThe mixture was then cooled
- customthe solids removed
- stirringthe resulting mixture was shaken overnight at room temperature
- concentrationThe solution was concentrated
- customan evaporator
- dissolutiondissolved in 1:1 AcOH
- filtrationH2O (5.0 mL) then an additional 2.0 ml AcOH, filtered
- custompurified by preparative HPLC
Sources & evidence
- ORD record
- ord-21939524e57f442fb56cf51e501b04c2
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08530663B2
Reaction notes
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