تفاعل #69917

معادلة التفاعل

TFA

4-[2-(Toluene-4-sulfonyloxymethyl)furan-3-yl]piperidine-1-carboxylic acid t-butyl ester

potassium carbonate

3-chlorophenol

→

title compound

4-[3-(3-Chlorophenoxymethyl)furan-2-yl]piperidine

TFA

المردود 98.0%

المذيبات

MeCN

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was then cooled
2. 2
   أخرىthe solids removed
3. 3
   workup.STIRRINGthe resulting mixture was shaken overnight at room temperature
4. 4
   تركيزThe solution was concentrated
5. 5
   أخرىan evaporator
6. 6
   workup.DISSOLUTIONdissolved in 1:1 AcOH
7. 7
   ترشيحH2O (5.0 mL) then an additional 2.0 ml AcOH, filtered
8. 8
   أخرىpurified by preparative HPLC

الإجراء التجريبي

4-[2-(Toluene-4-sulfonyloxymethyl)furan-3-yl]piperidine-1-carboxylic acid t-butyl ester (65 mg, 0.15 mmol was dissolved in MeCN (770 μL) and added to a mixture of potassium carbonate (32 mg, 230 mmol, 1.6 eq.) and 3-chlorophenol (28.8 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 (4.3 mg, 98% purity). MS m/z: [M+H]+ calcd for C16H18ClNO2, 292.10. found 292.0.

المصدر