Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | P-Toluenesulfonamide | HCID 6269 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Product | 15023-39-9 | HCID 17851595 | — |
Reaction Steps
reacting an iodolactone of the formula ##STR60## with thionyl chloride and treating with ammonia to yield a primary amide of the formula ##STR61## treating the primary amide with hydroxy (tosyloxy) iodobenzene to yield a p-toluenesulfonic acid salt of the formula ##STR62## tosylating the p-toluenesulfonic acid salt with toluenesulfonyl chloride in pyridine to yield a tosylamine of the formula ##STR63## treating the tosylamine with zinc in acetic acid to yield a norbornene carboxylic acid of the formula ##STR64## treating the norbornene carboxylk acid sequentially with ozone and with sodium borohydride and an acidic workup to yield a gamma-lactone of the formula ##STR65## performing ammonolysis of the gamma-lactone to afford a primary amide diol of the formula ##STR66## reducing and protecting the amine with BOC to produce a tert-butyl carbamate diol of the formula ##STR67## and sequentially treating the tert-butyl carbamate diol with toluenesulfonyl chloride, trifluoroacetic acid and diisopropylethylamine to produce a tosylamine azanoradamantane of the formula ##STR68##
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05717098 |
|---|
| Source dataset | uspto-grants-1998_02 |
|---|
| ORD ID | ord-81987366c0674a188fda65373e8ab612 |
|---|
| Source note | uspto-grants-1998_02 |
|---|
