Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-Oxo-3-phenethyl-3,10-diaza-bicyclo[4.3.1]decane-10-carboxylic Acid tert-Butyl Ester

HRID 987095Notes

Reaction equation

HRID 987095 reaction equation
C([O:8][C:9]([N:11]1[CH:16]([C:17](=[O:27])[NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:28][CH:29](OC)OC)=[O:10])C1C=CC=CC=1.[C:34]1([CH3:44])[CH:39]=CC(S([O-])(=O)=O)=C[CH:35]=1.[NH+]1C=CC=CC=1.[H][H]>C1(C)C=CC=CC=1.[Pd]>[C:34]([O:8][C:9]([N:11]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:16]1[C:17](=[O:27])[N:18]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:29][CH2:28]2)=[O:10])([CH3:44])([CH3:39])[CH3:35]

Participants

6

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 545104932-(2,2-Dimethoxy-ethyl)-6-phenethylcarbamoyl-piperidine-1-carboxylic Acid Benzyl Ester2×HCID 178418361HCID 178418361, compound

Product 1

HCID 213637462-Oxo-3-phenethyl-3,10-diaza-bicyclo[4.3.1]decane-10-carboxylic Acid tert-Butyl EsterYield 1,177.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2-(2,2-Dimethoxy-ethyl)-6-phenethylcarbamoyl-piperidine-1-carboxylic acid benzyl ester (Compound 239, 0.297g, 0.65mmol) was dissolved in toluene (15 ml), and the flask was immersed in a 80° C. oil bath. Pyridinium p-toluene sulfonate (0.0120 g, 0.05 mmol) was added and the reaction was stirred at 80° C. for 2 hours. After this time, the reaction was cooled down and the precipitate formed was removed by filtration. The toluene was evaporated and the residue was dissolved in dioxane (10 mL). N-(tert-Butoxycarbonyl anhydride (0.285 g, 1.31 mmol) and palladium 10% on activated carbon (0.1 g) were added. Hydrogen was applied via Parr apparatus and reaction was shaken at 50 psi for 12 hours. The black suspension was then filtered through compacted Celite, and dioxane was removed. Flash chromatographic purification of the residue (1:2 EtOAc/hexanes) gave Compound 240 (0.211 g, 90%). Rf=0.31 (1:2 EtOAc/hexanes).

Workup

  1. customwas immersed in a 80° C.
  2. temperatureAfter this time, the reaction was cooled down
  3. customthe precipitate formed
  4. customwas removed by filtration
  5. customThe toluene was evaporated
  6. dissolutionthe residue was dissolved in dioxane (10 mL)
  7. stirringwas shaken at 50 psi for 12 hours
  8. filtrationThe black suspension was then filtered
  9. customwas removed
  10. customFlash chromatographic purification of the residue (1:2 EtOAc/hexanes)

Sources & evidence

ORD record
ord-4fcb28b9f7934b3e909e4c01fcf47843
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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