Реакция #586096

Уравнение реакции

ammonium formate

2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-one

ether

sodium cyanoborohydride

→

3-Amino-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octane

Растворители

methanol

Условия реакции

Обработка

1. 1
   workup.STIRRINGAfter stirring another hour at ambient temperature
2. 2
   workup.STIRRINGThe reaction was then stirred at ambient temperature overnight
3. 3
   Другоеterminated by addition of water (˜5 mL)
4. 4
   ДругоеThe quenched reaction
5. 5
   Другоеwas partitioned between 5 M NaOH (10 mL) and chloroform (20 mL)
6. 6
   ЭкстракцияThe aqueous layer was extracted with chloroform (20 mL)
7. 7
   Сушкаwere dried (Na2SO4)
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated
10. 10
    workup.ADDITIONa 90:10 mixture of the cis and trans amines

Методика

To a stirred solution of 2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-one (3.00 g, 13.9 mmol) in dry methanol (20 mL), under nitrogen, was added a 1 M solution of ZnCl2 in ether (2.78 mL, 2.78 mmol). After stirring at ambient temperature for 30 min, this mixture was treated with solid ammonium formate (10.4 g, 167 mmol). After stirring another hour at ambient temperature, solid sodium cyanoborohydride (1.75 g, 27.8 mmol) was added in portions. The reaction was then stirred at ambient temperature overnight and terminated by addition of water (˜5 mL). The quenched reaction was partitioned between 5 M NaOH (10 mL) and chloroform (20 mL). The aqueous layer was extracted with chloroform (20 mL), and combined organic layers were dried (Na2SO4), filtered and concentrated. This left 2.97 g of yellow gum. GC/MS analysis indicated that the product was a 90:10 mixture of the cis and trans amines, along with a trace of the corresponding alcohol (98% mass recovery).

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