Sodium Hydroxide → 1-(p-Chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride

HRID 2048994노트

반응식

HRID 2048994 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]12[C:17](=O)[NH:16][C:15](=O)[CH:14]1[CH2:13]2.[H-].COCCO[Al+]OCCOC.[Na+].[H-].[H-].[OH-].[Na+]>C1C=CC=CC=1.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]12[CH2:13][CH:14]1[CH2:15][NH:16][CH2:17]2

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 867362351-(p-Chloro-alpha,alpha,alpha-trifluoro-m-tolyl)cyclopropanedicarboximide

생성물 1

HCID 867362331-(p-Chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride

시약·촉매·용매 2

HCID 241Benzene용매HCID 3283Diethyl Ether용매

실험 절차

To a solution of 0.28 g of (1-(4-chloro-α,α,α-trifluoro-m-tolyl)cyclopropanedicarboximide in 10 ml of benzene is added 1.0 ml of sodium bis(2-methoxyethoxy)aluminum hydride (70% benzene solution). This is refluxed for one hour, cooled to ambient temperature, and the excess hydride reagent is decomposed with one ml of 10 N sodium hydroxide. The benzene layer is washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give an amber-colored oil. This is dissolved in ether and dry hydrogen chloride is bubbled into the solution. The resultant precipitate is collected by filtration and recrystallized from isopropyl alcohol to give 1-(4-chloro-α,α,α-trifluoro-m-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride. Purification of the hydrochloride by recrystallization from acetonitrile gives colorless crystals, m.p. 164°-166° C.

후처리

  1. temperatureThis is refluxed for one hour
  2. washThe benzene layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto give an amber-colored oil
  6. customdry hydrogen chloride is bubbled into the solution
  7. filtrationThe resultant precipitate is collected by filtration
  8. customrecrystallized from isopropyl alcohol

출처 및 근거

ORD 기록
ord-efc6cf24121e49cb977d5de61d3b403c
출처 데이터셋
uspto-grants-1980_04
특허 번호
US04196120

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