5-(4-Benzyloxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one → 5-(4-Hydroxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one

HRID 2269311Notes

Reaction equation

HRID 2269311 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH:22]3[CH2:24][CH2:25][CH:19]2[C:20](=[O:26])[O:21]3)(=[O:17])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C.CO>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH:22]3[CH2:24][CH2:25][CH:19]2[C:20](=[O:26])[O:21]3)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 183337695-(4-Benzyloxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 183336285-(4-Hydroxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-oneYield 104.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 5-(4-benzyloxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (1.0 g, 2.7 mmol), ethyl acetate-methanol (1:1, 100 mL) and 10% Pd on charcoal (0.22 g) was shaken under 50 psi of hydrogen for 1.5 h. Filtration through a pad of Celite and concentration of the filtrate in vacuo afforded 0.80 g of 5-(4-hydroxy-benzenesulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one as a colorless solid.

Workup

  1. filtrationFiltration through a pad of Celite and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-dd1fe54c168947938b20deb81fb5e566
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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