HCID 69597629, compound → HCID 45082134, compound

HRID 1796800Notes

Reaction equation

HRID 1796800 reaction equation
[CH3:1][C:2]1([CH3:19])[C@H:7]2[N:8](C(C3C=CC=CC=3)C)[CH2:9][C@H:4]([O:5][C:6]2=[O:18])[CH2:3]1.[H][H]>[Pd].CO>[CH3:1][C:2]1([CH3:19])[C@H:7]2[NH:8][CH2:9][C@H:4]([O:5][C:6]2=[O:18])[CH2:3]1

Participants

5

Reactant 2

HCID 69597629HCID 69597629, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 45082134HCID 45082134, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a small Parr shaker bottle was added of (1R,4R)-8,8-Dimethyl-5-(1-phenyl-ethyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXV, 1.04 g, 4.01 mmol), methanol (50 ml) and 0.12 g of 10% Palladium on charcoal. The mixture was shaken under about 50 psi of hydrogen for about 19 hours. The mixture was filtered and concentrated, affording 0.59 g of (1R,4R)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXVI) as a filmy solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-953d31955e28474eac17669a58cc62fc
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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