تفاعل #589618

معادلة التفاعل

4-(3-hydroxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester

potassium carbonate

rac-2,2-dimethyl-1,3-dioxolan-4-yl-methyl p-toluenesulfonate

→

title compound

المردود 71.1%

rac-4-[3-(2,2-Dimethyl-[1,31 dioxolan-4-ylmethoxy)-5-methoxy-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

المردود 71.1%

المذيبات

MeCN

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for 22 hours
2. 2
   workup.ADDITIONpoured
3. 3
   استخلاصextracted twice with EtOAc
4. 4
   غسيلThe organic phases were washed with water and brine
5. 5
   تجفيفdried over MgSO4
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated i.V
8. 8
   أخرىand the residue (2.11 g) was purified by chromatography (SiO2, MeCl2/MeOH)

الإجراء التجريبي

1.60 g (4.6 mmol) of 4-(3-hydroxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester (example 168a) was dissolved in 50 ml of MeCN at rt; 1.29 g (9.4 mmol) of anhydrous potassium carbonate was added, followed by 1.495 g (4.8 mmol) of rac-2,2-dimethyl-1,3-dioxolan-4-yl-methyl p-toluenesulfonate. The reaction mixture was stirred at reflux for 22 hours. It was then cooled down to ambient temperature and poured into crashed ice and extracted twice with EtOAc. The organic phases were washed with water and brine, dried over MgSO4, filtered and evaporated i.V. and the residue (2.11 g) was purified by chromatography (SiO2, MeCl2/MeOH) to yield 1.52 g of the title compound as a colorless amorphous solid. MS: 465.2 (MH+).

المصدر