3-(2-Benzyloxyethyl)-2-oxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester → 3-(2-Benzyloxy-ethyl)-3,9-diaza-bicyclo[3.3.1]nonan-2-one

HRID 987083Notes

Reaction equation

HRID 987083 reaction equation
C(OC([N:11]1[CH:16]2[CH2:17][CH2:18][CH2:19][CH:12]1[C:13](=[O:30])[N:14]([CH2:20][CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:15]2)=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH2:23]([O:22][CH2:21][CH2:20][N:14]1[CH2:15][CH:16]2[NH:11][CH:12]([CH2:19][CH2:18][CH2:17]2)[C:13]1=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 544963693-(2-Benzyloxyethyl)-2-oxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester2×HCID 178418361HCID 178418361, compound

Product 1

HCID 229878873-(2-Benzyloxy-ethyl)-3,9-diaza-bicyclo[3.3.1]nonan-2-oneYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(2-Benzyloxyethyl)-2-oxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound 5, 0.15 g, 0.36 mmol) was dissolved in MeOH (5 mL), and palladium (10%) on activated carbon (0.03 g) was added. Hydrogen was applied via balloon for 1 hour. The black suspension was then filtered through compacted Celite, and the methanol was removed by high-vacuum rotary evaporator to give Compound 6 (0.09 g, 90%) as a thick oil, which was of sufficiently good quality to be advanced to the coupling reaction without further purification.

Workup

  1. filtrationThe black suspension was then filtered
  2. customthe methanol was removed by high-vacuum rotary evaporator

Sources & evidence

ORD record
ord-926130508f63407a95a4d9b8a63e6083
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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