Реакция #159324

Уравнение реакции

Boc-nortropinone

NaCNBH3

→

tert-butyl 3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate

Выход 98.9%

Растворители

MeOH

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat reflux for 2 h
3. 3
   КонцентрированиеThe mixture was concentrated
4. 4
   workup.ADDITIONthe residue was diluted with 0.5 M aq NaOH (30 mL)
5. 5
   Экстракцияextracted with CH2Cl2 (2×50 mL)
6. 6
   ПромывкаThe combined organic phase was washed with brine (20 mL)
7. 7
   Сушкаdried over Na2SO4
8. 8
   Концентрированиеconcentrated

Методика

A stirred mixture of Boc-nortropinone (287 mg, 1.3 mmol), NH4OAc (1.96 g, 25.5 mmol), NaCNBH3 (800 mg, 12.7 mmol) and MeOH (20 mL) was heated at reflux for 2 h. The mixture was concentrated, the residue was diluted with 0.5 M aq NaOH (30 mL) and extracted with CH2Cl2 (2×50 mL). The combined organic phase was washed with brine (20 mL), dried over Na2SO4 and concentrated to afford tert-butyl 3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate (291 mg, quant) as a mixture of isomers. LC-MS Method 1 tR=0.88 min, m/z=227.

Источник