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 987095ノート

反応式

HRID 987095 の反応式
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]

参加物

6

反応物 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 回HCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4fcb28b9f7934b3e909e4c01fcf47843
出典データセット
uspto-grants-2003_10
特許番号
US06630472B1

反応ノート

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