Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | o-Toluenesulfonyl chloride | HCID 8623 | — |
| Product | P-Toluenesulfonamide | HCID 6269 | — |
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 |
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| Source dataset | uspto-grants-1998_02 |
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| ORD ID | ord-6707e6eea9e84c3991144ba223376f04 |
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| Source note | uspto-grants-1998_02 |
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