HCID 69597614, compound → HCID 69597672, compound

HRID 1796802Notes

Reaction equation

HRID 1796802 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][C@H:22]3[CH2:24][C:25]([CH3:27])([CH3:26])[C@@H:19]2[C:20](=[O:28])[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][C@H:22]3[CH2:24][C:25]([CH3:26])([CH3:27])[C@@H:19]2[C:20](=[O:28])[O:21]3)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 69597614HCID 69597614, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 69597672HCID 69597672, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of (1R,4R)-5-(4-benzyloxy-benzenesulfonyl)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXVII, 3.7 g, 9.3 mmol), 10% palladium on charcoal (0.8 g) and 470 ml of 1:1 ethyl acetate-methanol was stirred for about 1.5 hours under about 50 psi of hydrogen gas. The mixture was filtered through a pad of Celite®. Concentration of the filtrate afforded 2.4 g (1R,4R)-5-(4-hydroxy-benzenesulfonyl)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXVIII) as a colorless solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®

Sources & evidence

ORD record
ord-41f6d49ad4034c29822cce35860e5cdf
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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