HuagongsheHuagongshe Chemistry Print Report · For research reference only
Azide → Methyl 2-[1-(aminomethyl)cyclohexyl]acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Azide | HCID 33558 | — |
| Reactant | Isocyanate | HCID 105034 | — |
| Reactant | 1,1-Cyclohexanediacetic acid mono methyl ester | HCID 11572043 | — |
| Product | Methyl 2-[1-(aminomethyl)cyclohexyl]acetate | HCID 21692047 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06384069B1 |
| Source dataset | uspto-grants-2002_05 |
| ORD ID | ord-4c68d9da1eb3420bb3047e6a1a7fc7e7 |
| Source note | uspto-grants-2002_05 |