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 987095노트

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HRID 987095 반응식
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]

참가 물질

6

반응물 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 545104932-(2,2-Dimethoxy-ethyl)-6-phenethylcarbamoyl-piperidine-1-carboxylic Acid Benzyl Ester2회HCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4fcb28b9f7934b3e909e4c01fcf47843
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630472B1

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