반응 #1886971

반응 방정식

3,3-difluoro-N,N-dimethylcyclobutanecarboxamide

lithium aluminum hydride

→

1-(3,3-difluorocyclobutyl)-N,N-dimethylmethanamine

수율 54.7%

용매

THF

THF

반응 조건

후처리

1. 1
   기타to come to RT
2. 2
   기타it was quenched
3. 3
   workup.ADDITIONby slowly adding 10 mL 6 N NaOH and 5 mL water at 5° C.
4. 4
   workup.STIRRINGwith stirring
5. 5
   workup.STIRRINGThe mixture was stirred at RT for 0.5 h
6. 6
   건조dried over Na2SO4
7. 7
   여과filtered
8. 8
   농축The filtrate was concentrated to ca. 30 mL by a careful distillation of most of the THF using a Vigreux column
9. 9
   workup.DISTILLATIONThe remaining material was distilled under slightly reduced pressure (ca. 100-200 mm Hg)
10. 10
    기타the fraction (20 mL, by 70-90° C.)
11. 11
    기타The residual THF was carefully purged with a gentle stream of nitrogen

실험 절차

A solution of 3,3-difluoro-N,N-dimethylcyclobutanecarboxamide (24 g, 147 mmol) prepared in Part A in THF (500 mL) was added to a stirred suspension of lithium aluminum hydride (7.5 g, 198 mmol) in 500 mL THF at 0° C. The mixture was allowed to come to RT. After stirring the reaction mixture at RT for 18 h, it was quenched by slowly adding 10 mL 6 N NaOH and 5 mL water at 5° C. with stirring. The mixture was stirred at RT for 0.5 h, dried over Na2SO4 and filtered. The filtrate was concentrated to ca. 30 mL by a careful distillation of most of the THF using a Vigreux column. The remaining material was distilled under slightly reduced pressure (ca. 100-200 mm Hg); the fraction (20 mL, by 70-90° C.) contained the title compound contaminated with THF. The residual THF was carefully purged with a gentle stream of nitrogen to yield 1-(3,3-difluorocyclobutyl)-N,N-dimethylmethanamine (12 g, 80 mmol, 54.7% yield). 1H NMR (400 MHz, CDCl3) δ 2.46-2.94 (2H, m), 2.38 (2H, d, J=6.55 Hz), 2.16-2.28 (9H, m).

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