Acetic Acid → 15023-39-9

HRID 862157Notes

Reaction equation

HRID 862157 reaction equation
S(N)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=O)=O.[C:12]([OH:15])(=[O:14])C>[Zn]>[C:4]12([C:12]([OH:15])=[O:14])[CH2:8][CH:7]([CH2:9][CH2:10]1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 6269P-Toluenesulfonamide

Product 1

HCID 1785159515023-39-9

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

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-81987366c0674a188fda65373e8ab612
Source dataset
uspto-grants-1998_02
Patent number
US05717098

Reaction notes

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