Sodium Hydroxide → 1-(p-Chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride
Reaction equation
[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]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- temperatureThis is refluxed for one hour
- washThe benzene layer is washed with water
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
- customto give an amber-colored oil
- customdry hydrogen chloride is bubbled into the solution
- filtrationThe resultant precipitate is collected by filtration
- customrecrystallized from isopropyl alcohol
Sources & evidence
- ORD record
- ord-dce3dbbccce54e3fa3455c584695f261
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04231935
Reaction notes
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