Реакция #164576

Уравнение реакции

methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)5-nitroisonicotinate

Methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)5-nitroisonicotinate

Intermediate 27A

Methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)5-nitroisonicotinate

lithium hydroxide

methanol

water

→

2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-nitroisonicotinic acid

Выход 55.6%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   КонцентрированиеThe reaction mixture was concentrated
2. 2
   Другоеpurified by a 50 g silica column
3. 3
   Промывкаeluting with 10-40% methanol in DCM

Методика

To a solution of methyl 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)5-nitroisonicotinate (Intermediate 27A) (6.0 g, 19.6 mmol) in tetrahydrofuran (15 mL) under nitrogen was added lithium hydroxide (2.47 g, 58.8 mmol), methanol (10 mL) and water (15 mL), reaction then stirred overnight. The reaction mixture was concentrated and purified by a 50 g silica column eluting with 10-40% methanol in DCM to afford 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-nitroisonicotinic acid (3.2 g, 10.9 mmol).

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