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

HRID 987086Notes

Reaction equation

HRID 987086 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]([C:17]([OH:19])=O)[CH2:15][CH2:14][CH2:13][CH:12]1[C:20]([OH:22])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([CH2:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OC(=O)C)(=O)C>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:16]1[C:17](=[O:19])[N:33]([CH2:32][CH2:31][CH2:30][CH2:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20]2=[O:22])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 83242BenzenebutanamineHCID 12265926Piperidine-1,2,6-tricarboxylic acid 1-benzyl ester

Product 1

HCID 537413262,4-Dioxo-3-(4-phenylbutyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl EsterYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Anhydride 2 (0.54 g, 1.89 mmol, prepared from Compound 1) was dissolved in 1 mL of dioxane. 4-Phenylbutylamine (0.28 g, 1.89 mmol) was added from the top. The mixture was stirred at room temperature for 1 hour. After this time, acetic anhydride (0.62 mL, 3.78 mmol) was added, and the reaction was refluxed for 5 hours. The dioxane was evaporated, and flash chromatographic purification of the residue (40% EtOAc/hexanes) gave Compound 13 (0.75 g, 95% yield) as a colorless thick oil. Rf=0.66 (40% EtOAc/hexanes); IR: 2935, 2863, 1710, 1688, 1430, 1341, 1311, 1256, 1126, 1096, 1069, 749, 699 cm−1; 1H NMR: δ 1.41-2.04 (m, 8H), 2.61 (t, 2H, J=6.9), 3.79 (t, 2H, J=6.9), 4.96 (s, 2H), 5.14 (s, 2H), 7.14-7.37 (m, 10H).

Workup

  1. temperaturethe reaction was refluxed for 5 hours
  2. customThe dioxane was evaporated
  3. customflash chromatographic purification of the residue (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-24c500cd7a694704b866355ca5b159f2
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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