Water → 3-Cyclopropylcarbonyl-1-phenyl-3-azabicyclo[3.1.0]hexane

HRID 66275Notes

Reaction equation

HRID 66275 reaction equation
[C:1]1([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13]1([C:16](Cl)=[O:17])[CH2:15][CH2:14]1.O>C1C=CC=CC=1.C(N(CC)CC)C>[CH:13]1([C:16]([N:9]2[CH2:10][CH:11]3[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([CH2:12]3)[CH2:8]2)=[O:17])[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 101300941-Phenyl-3-azabicyclo[3.1.0]hexane

Product 1

HCID 128913673-Cyclopropylcarbonyl-1-phenyl-3-azabicyclo[3.1.0]hexane

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred slurry of 61.2 g of 1-phenyl-1,2-cyclopropanedicarboximide (U.S. Pat. No. 3,166,571-Example VIII) in 2 liters of benzene is added 400 ml of sodium bis(2-methoxyethoxy)aluminum hydride 70% solution in benzene under nitrogen. The mixture is stirred at room temperature for 2 hours, refluxed for 4 hours and then stirred at room temperature for 20 hours. A 400 ml portion of 10N sodium hydroxide is added cautiously with stirring. The organic layer is washed twice with dilute sodium hydroxide and then with water, dried over magnesium sulfate and evaporated to give an amber oil. This oil is dissolved in dilute hydrochloric acid, washed with ether, filtered and the filtrate made basic with sodium hydroxide. The basic filtrate is extracted with benzene, dried over magnesium sulfate, filtered and evaporated to give 1-phenyl-3-azabicyclo[3.1.0]hexane as an amber oil. To a solution of 15.9 g of 1-phenyl-3-azabicyclo[3.1.0]hexane in 100 ml of benzene and 20 ml of triethylamine is added 11.0 g of cyclopropanecarboxylic acid chloride in 20 ml of benzene over 5 minutes. The mixture is stirred for 30 minutes and 50 ml of water is added. The benzene layer is extracted with dilute sodium bicarbonate followed by dilute hydrochloric acid and then water, dried over magnesium sulfate and evaporated to give the product 3-cyclopropylcarbonyl-1-phenyl-3-azabicyclo[3.1.0]hexane as a brown oil.

Workup

  1. extractionThe benzene layer is extracted with dilute sodium bicarbonate
  2. dry with materialwater, dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-aa9dfd64c8944fa6a7004e0665203826
Source dataset
uspto-grants-1978_12
Patent number
US04131611

Reaction notes

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