تفاعل #167730

معادلة التفاعل

4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoic acid

4-(1-pyrrolidinyl)piperidine

1-hydroxybenzotriazole

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

→

boronic acid

المردود 42.0%

[4-(pyrrolidin-1-yl)piperidin-1-yl][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone

المردود 42.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىUpon removal of DMF on rotavap
2. 2
   workup.ADDITIONthe residue was taken into mixture of EtOAc and H2O
3. 3
   استخلاصThe combined organic layers from extraction
4. 4
   أخرىthe aqueous layer was purified by reverse phase prep-HPLC

الإجراء التجريبي

A solution of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoic acid (9.80 mmol, 2.43 g), 4-(1-pyrrolidinyl)piperidine (10.77 mol, 1.66 g), 1-hydroxybenzotriazole (16.67 mmol, 2.25 g), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (19.57 mmol, 3.75 g) in DMF (30 mL) was stirred overnight at 60° C. Upon removal of DMF on rotavap, the residue was taken into mixture of EtOAc and H2O. The combined organic layers from extraction were stirred with aq. 2N HCl for 20 min and the aqueous layer was purified by reverse phase prep-HPLC to furnish the desired boronic acid (1.24 g. 42%).

المصدر