Tert-butyl 9-benzyl-7-oxo-3,9-diazabicyclo[3.3.1]nonane-3-carboxylate → 3-Boc-7-oxo-3,9-diazabicyclo[3.3.1]nonane

HRID 1393222Notes

Reaction equation

HRID 1393222 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16](CC3C=CC=CC=3)[CH:10]([CH2:11][C:12](=[O:24])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[NH:16][CH:10]([CH2:11][C:12](=[O:24])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 59679479Tert-butyl 9-benzyl-7-oxo-3,9-diazabicyclo[3.3.1]nonane-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 596794733-Boc-7-oxo-3,9-diazabicyclo[3.3.1]nonaneYield 99.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

9-Benzyl-7-oxo-3,9-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (16.6 g, 50.5 mmol) was dissolved in methanol (40 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 (40 psi) and evacuated three times. The Parr bottle was refilled with hydrogen (40 psi) and shook for 48 h. The suspension was filtered through Celite and concentrated under vacuum to give 12.1 g (quantitative yield) of 7-oxo-3,9-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester as a yellow oil. Retention time (min)=0.531, method [1], MS(ESI) 481.3 (2M+H).

Workup

  1. customevacuated three times
  2. additionThe Parr bottle was refilled with hydrogen (40 psi)
  3. filtrationThe suspension was filtered through Celite
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3902b579c1284dec84bd8d56513435cb
Source dataset
uspto-grants-2008_03
Patent number
US07345056B2

Reaction notes

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