2,4-Dioxo-3-(4-phenylbutyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester → 3-(4-Phenylbutyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione

HRID 987087Notes

Reaction equation

HRID 987087 reaction equation
C(OC([N:11]1[CH:16]2[CH2:17][CH2:18][CH2:19][CH:12]1[C:13](=[O:31])[N:14]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:15]2=[O:20])=O)C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[C:25]1([CH2:24][CH2:23][CH2:22][CH2:21][N:14]2[C:15](=[O:20])[CH:16]3[NH:11][CH:12]([CH2:19][CH2:18][CH2:17]3)[C:13]2=[O:31])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 537413262,4-Dioxo-3-(4-phenylbutyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester2×HCID 178418361HCID 178418361, compound

Product 1

HCID 229879053-(4-Phenylbutyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dioneYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dioxo-3-(4-phenylbutyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound 13, 0.57 g, 1.36 mmol) was dissolved in THF (3 mL), and 10% palladium on activated carbon (0.12 g) was added. Hydrogen was applied via balloon for 1 hour. The black suspension was then filtered through compacted Celite, and the THF was removed by high-vacuum rotary evaporator to give Compound 14 (0.36 g, 92%) as a thick oil, which was of sufficiently good quality to be advanced to the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-bce372b42ea744fd83e0f4949e6387d1
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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