HuagongsheHuagongshe Chemistry Print Report · For research reference only
8-Methyl-8-azabicyclo(3.2.1)octan-3-ol → 3-Chloro-8-methyl-8-azabicyclo(3.2.1)octane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 8-Methyl-8-azabicyclo(3.2.1)octan-3-ol | HCID 8424 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | Npc164516 | HCID 79038 | — |
| Reactant | Tosylmethyl isocyanide | HCID 161915 | — |
| Reactant | 8-Methyl-8-azabicyclo[3.2.1]octane-3-carbonitrile | HCID 557623 | — |
| Reactant | Potassium ethoxide | HCID 23670592 | — |
| Product | 3-Chloro-8-methyl-8-azabicyclo(3.2.1)octane | HCID 137527 | — |
Reaction Steps
3-Cyano-8-methyl-8-azabicyclo[3.2.1]octane (IV) can be prepared by treating tropinone (V) with tosylmethyl isocyanide in the presence of a suitable base, such as potassium ethoxide. As an alternative 3-cyano-8-methyl-8-azabicyclo[3.2.1]octane (IV) can be prepared from tropine (XII) by treatment with thionyl chloride to give alternative 3-chloro-8-methyl-8-azabicyclo[3.2.1]octane (XIII) followed by treatment with cyanide as described in J. Am. Chem. Soc., 1958 80, 4677.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06573275B1 |
| Source dataset | uspto-grants-2003_06 |
| ORD ID | ord-31d4b9e708fa4561b055757f99d5637f |
| Source note | uspto-grants-2003_06 |