HCID 67373504, compound → HCID 67387779, compound

HRID 1971916Notes

Reaction equation

HRID 1971916 reaction equation
[CH3:1][N:2]1[CH:7]2[CH:8]([O:10][C:11](=[O:13])[CH3:12])[CH2:9][C@@H:3]1[CH2:4][C:5](=[O:14])[CH2:6]2>C(O)C.[Pt](=O)=O>[OH:14][C@@H:5]1[CH2:6][CH:7]2[N:2]([CH3:1])[CH:3]([CH2:9][C@H:8]2[O:10][C:11](=[O:13])[CH3:12])[CH2:4]1

Participants

4

Reactant 1

HCID 67373504HCID 67373504, compound

Product 1

HCID 67387779HCID 67387779, compoundYield 119.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of the above ester (4.11 mmol, 0.811 g) in 95% ethanol (50 mL) was added platinum (IV) oxide (0.354 mmol, 0.081 g), and the reaction was pressurized to 50 psi of H2. The reaction was stirred vigorously for 12 hours. The reaction was filtered through a pad of celite and the celite was washed with portions of ethyl acetate. The solvents were removed under reduced pressure to provide acetic acid (3S,6R)-3-hydroxy-8-methyl-8-aza-bicyclo[3.2.1]oct-6-yl ester (0.98 g) which was used without further purification in the next step.

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. washthe celite was washed with portions of ethyl acetate
  3. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-e9eeb43b06c447999e19d8f1d1abb6cd
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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