Pyridine → P-Toluenesulfonamide
Reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1(C)C(S(Cl)(=O)=O)=CC=CC=1.[N:23]1C=CC=CC=1>>[S:7]([NH2:23])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]Participants
Procedure
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##
Sources & evidence
- ORD record
- ord-6707e6eea9e84c3991144ba223376f04
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05717098
Reaction notes
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