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

HRID 1934536Notes

Reaction equation

HRID 1934536 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.

Sources & evidence

ORD record
ord-4c68d9da1eb3420bb3047e6a1a7fc7e7
Source dataset
uspto-grants-2002_05
Patent number
US06384069B1

Reaction notes

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