HCID 59679476, compound → HCID 59679469, compound

HRID 1393214Notes

Reaction equation

HRID 1393214 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:13][CH:12]2[N:14](CC3C=CC=CC=3)[CH:8]([CH2:9][C:10](=[O:22])[CH2:11]2)[CH2:7]1)=[O:5])[CH3:2].[H][H]>CO.[OH-].[Pd+2].[OH-]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:13][CH:12]2[NH:14][CH:8]([CH2:9][C:10](=[O:22])[CH2:11]2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 59679476HCID 59679476, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59679469HCID 59679469, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

9-Benzyl-7-oxo-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid ethyl ester (11.1 g, 36.8 mmol) was dissolved in methanol (30 mL) and added to a suspension of palladium hydroxide (1 g) in methanol (10 mL) in a Parr bottle. The Parr bottle was filled with hydrogen (30 psi) and evacuated three times. The Parr bottle was refilled with hydrogen (30 psi) and shook for 12 h. The suspension was filtered through Celite and concentrated under vacuum to give 7.81 g (quantitative yield) of 7-oxo-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid ethyl ester as a yellow oil. Retention time (min)=0.369, method [1], MS(ESI) 212.1 (M+H).

Workup

  1. customevacuated three times
  2. additionThe Parr bottle was refilled with hydrogen (30 psi)
  3. filtrationThe suspension was filtered through Celite
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-547c2a59a2424f9c90ecd1876a63c27f
Source dataset
uspto-grants-2008_03
Patent number
US07345056B2

Reaction notes

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