Water → HCID 23332365, compound

HRID 224301Notes

Reaction equation

HRID 224301 reaction equation
[CH2:1]1[C:3]2([C:9]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=3)[C:4]([NH:6][C:7](=O)[CH:2]12)=O.[CH2:16]([Mg]Br)[CH3:17].O>CCOCC>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:3]23[CH2:1][CH:2]2[CH:7]([CH2:16][CH3:17])[NH:6][CH2:4]3)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27361CiproximidaHCID 178418443HCID 178418443, compound

Product 1

HCID 23332365HCID 23332365, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 4.43 g of 1-(p-chlorophenyl)-1,2-cyclopropanedicarboximide in 100 ml of ether is added 16.4 ml of 2 M ethylmagnesium bromide. The mixture is allowed to stand at room temperature for 18 hours and then is combined with water. The ether solution is dried over sodium sulfate and evaporated to give 4.05 g of a pink semisolid. Crystallization from ether hexane gives 1-(p-chloropehnyl)-4-ethyl-4-hydroxy-3-azabicyclo[3.1.0]hexan-2-one as colorless crystals, m.p. 154°-157° C.

Workup

  1. dry with materialThe ether solution is dried over sodium sulfate
  2. customevaporated

Sources & evidence

ORD record
ord-ebc122a030ae45959b82637c8f7f2511
Source dataset
uspto-grants-1980_11
Patent number
US04231935

Reaction notes

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