Azide → Methyl 2-[1-(aminomethyl)cyclohexyl]acetate

HRID 1610933Notes

Reaction equation

HRID 1610933 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1([CH2:11]C(O)=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[N-:16]=[N+]=[N-].[N-]=C=O>>[NH2:16][CH2:11][C:5]1([CH2:4][C:3]([O:2][CH3:1])=[O:15])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 33558Azide2×HCID 105034Isocyanate2×HCID 115720431,1-Cyclohexanediacetic acid mono methyl ester

Product 1

HCID 21692047Methyl 2-[1-(aminomethyl)cyclohexyl]acetate

Procedure

1,1-Cyclohexanediacetic acid monomethyl ester is converted via the corresponding acid chloride into the azide. The azide is degraded by the Curtius method to the isocyanate. The isocyanate is then hydrolyzed to give methyl 1-aminomethyl-1-cyclohexaneacetate. Heating this substance in alkaline methanol under reflux for three days affords 8-azaspiro[5,4]decan-9-one or gabapentin lactam. GBP-L was characterized by means of Thin Layer Chromatography, Infrared-Spectroscopy, [1H]-NMR and [13C]-NMR (Nuclear Magnetic Resonance Spectroscopy) and FAB-MS (Fast Atom Bombardment Mass Spectroscopy).

Sources & evidence

ORD record
ord-b3ae4c40b102472b91c466a508203172
Source dataset
uspto-grants-2006_01
Patent number
US06984659B2

Reaction notes

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