تفاعل #1803747

معادلة التفاعل

NaOH

4-(2-amino-4-methyl-phenylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

cyclopropanecarboxaldehyde

Oxone

→

4-(2-cyclopropyl-5-methyl-benzoimidazol-1-yl)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

المردود 37.2%

المذيبات

H2O DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGAfter stirring for 5 minutes
2. 2
   استخلاصthe aqueous layer was extracted four times with ethyl acetate
3. 3
   غسيلThe combined organic extracts were washed twice with water, once with brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe residue was purified by flash chromatography (4/1 ethyl acetate/hexanes)

الإجراء التجريبي

To a solution of 4-(2-amino-4-methyl-phenylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2 g, 6.23 mmol) and cyclopropanecarboxaldehyde (485 μL, 6.5 mmol) in a 3% H2O/DMF (10 mL) solution was added Oxone® (3.05 g, 4.96 mmol). The mixture was stirred for 1 h and poured into a 0.2 N NaOH solution (25 mL). After stirring for 5 minutes, the aqueous layer was extracted four times with ethyl acetate. The combined organic extracts were washed twice with water, once with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (4/1 ethyl acetate/hexanes) to yield 4-(2-cyclopropyl-5-methyl-benzoimidazol-1-yl)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (860 mg, 37%).

المصدر