Benzylamine → 3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione

HRID 2052220Notes

Reaction equation

HRID 2052220 reaction equation
C12CC1CNC2.C12CC1CNC2C(O)=O.[C@@H:16]1([C:22]([OH:24])=O)[CH2:18][C@@H:17]1[C:19](O)=[O:20].[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([N:32]1[C:22](=[O:24])[CH:16]2[CH:17]([CH2:18]2)[C:19]1=[O:20])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 7504BenzylamineHCID 726455cis-1,2-Cyclopropanedicarboxylic acidHCID 37794533-Azabicyclo[3.1.0]hexane-2-carboxylic acidHCID 131505233-Azabicyclo[3.1.0]hexane

Product 1

HCID 27645863-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione

Procedure

3-Azabicyclo(3.1.0)hexane, a precursor for preparing 3-azabicyclo(3.1.0)hexane-2-carboxylic acid, a plant gametocide, is prepared by (a) treating cis-1,2-cyclopropanedicarboxylic acid with benzylamine, to form 3-(benzyl)-3-azabicyclo(3.1.0)hexane-2,4-dione, (b) selectively reducing the dione to 3-(benzyl)-3-azabicyclo(3.1.0)hexane, and (c) hydrogenolysis of that compound to 3-azabicyclo(3.1.0)hexane.

Sources & evidence

ORD record
ord-a78236e8d59740808417ec75df9d4b6f
Source dataset
uspto-grants-1980_01
Patent number
US04183857

Reaction notes

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