Water → HCID 23332365, compound

HRID 66298Notes

Reaction equation

HRID 66298 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 2M 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-82d4ce6ae1594563b45e79f582a49292
Source dataset
uspto-grants-1978_12
Patent number
US04131611

Reaction notes

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