تفاعل #159611

معادلة التفاعل

3-Hydroxyazetidine hydrochloride

triethylamine

3-Hydroxyazetidine hydrochloride

triethylamine

Methyl 2,5-dichloronicotinate

→

title compound ( D62 )

المردود 76.6%

methyl 5-chloro-2-(3-hydroxyazetidin-1-yl)nicotinate

المردود 76.6%

المذيبات

tetrahydrofuran methanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   أخرىat 62° C.
3. 3
   أخرىovernight
4. 4
   درجة الحرارةthe reaction mixture was further heated at 80° C. for 28 h
5. 5
   أخرىSolvents were evaporated in vacuo
6. 6
   ترشيحThe formed solid was filtered
7. 7
   غسيلwashed with water (500 ml)
8. 8
   أخرىdried in vacuum

الإجراء التجريبي

To a mixture of 3-Hydroxyazetidine hydrochloride (37.17 g, 0.339 mol) and triethylamine (70.93 ml, 0.508 mol) in tetrahydrofuran/methanol (840/280 ml) Methyl 2,5-dichloronicotinate (70 g, 0.339 mol) was added and the resulting mixture was heated at 75° C. for 4 hours then at 62° C. overnight. 3-Hydroxyazetidine hydrochloride (3.7 g, 0.03 mol) and triethylamine (23.60 ml, 0.16 mol) were added and the reaction mixture was further heated at 80° C. for 28 h. Solvents were evaporated in vacuo. The residue was taken in dichloromethane (400 ml) and water (500 ml). The formed solid was filtered, washed with water (500 ml) and dried in vacuum to afford a first batch of the title compound (D62) (63 g).

المصدر