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

HRID 66287ノート

反応式

HRID 66287 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 3283Diethyl Ether溶媒

実験手順

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 10N 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.

後処理

  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

出典と根拠

ORDレコード
ord-2919bbeeaa34461598b3b7a927536eb9
出典データセット
uspto-grants-1978_12
特許番号
US04131611

反応ノート

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