تفاعل #2431

معادلة التفاعل

bromide

Methyl 3-(5-bromopentanoylamino)benzoate

NaH

→

oil

المردود 56.2%

Methyl 3-(2-oxo-1-piperidinyl)benzoate

المردود 56.2%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONKI (80 mg) added
2. 2
   درجة الحرارةthe mixture heated at 70° C. for 4 h
3. 3
   أخرىThe mixture was evaporated
4. 4
   أخرىpartitioned between EtOAc and 1M HCl
5. 5
   غسيلThe organic portion was washed with 5% KHCO3 and brine
6. 6
   ترشيحfiltered (Whatman® 1 PS, phase separator)
7. 7
   أخرىevaporated
8. 8
   أخرىThe residue was chromatographed (eluant 2% MeOH in EtOAc)

الإجراء التجريبي

The bromide of Example 36 (1.50 g, 4.88 mmol) was taken up in dry DMF (40 ml) and treated with NaH (160 mg, 80% disp. in oil) at 0° C. The mixture was stirred at r.t. under nitrogen for 10 min, then KI (80 mg) added and the mixture heated at 70° C. for 4 h. The mixture was evaporated and partitioned between EtOAc and 1M HCl. The organic portion was washed with 5% KHCO3 and brine, filtered (Whatman® 1 PS, phase separator) and evaporated. The residue was chromatographed (eluant 2% MeOH in EtOAc) to provide a colourless oil (640 mg, 56%).

المصدر