Potassium Iodide → [1-(4-Methyl-3-pentenyl)piperidin-4-yl] 2-cyclobutyl-2-hydroxy-2-phenylacetate

HRID 1289807ノート

反応式

HRID 1289807 の反応式
Cl.[CH:2]1([C:6]([OH:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]([O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:8])[CH2:5][CH2:4][CH2:3]1.Br[CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH:2]1([C:6]([OH:22])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:7]([O:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[CH2:14][CH2:15]2)=[O:8])[CH2:5][CH2:4][CH2:3]1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1375215-Bromo-2-methyl-2-penteneHCID 69831797(Piperidin-4-yl) 2-cyclobutyl-2-hydroxy-2-phenylacetate hydrochloride

生成物 1

HCID 18922143[1-(4-Methyl-3-pentenyl)piperidin-4-yl] 2-cyclobutyl-2-hydroxy-2-phenylacetate収率 61.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

50 mg of (piperidin-4-yl) 2-cyclobutyl-2-hydroxy-2-phenylacetate hydrochloride, 25 mg of 5-bromo-2-methyl-2-pentene, 25 mg of potassium iodide and 47 mg of anhydrous potassium carbonate were suspended in 5 ml of anhydrous N,N-dimethylformamide, and this suspension was stirred at 70° C. for 3 hours. The reaction mixture was cooled to room temperature, mixed with water, and then extracted with diethyl ether. The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol=20/1) to obtain 35 mg of the title compound.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol=20/1)

出典と根拠

ORDレコード
ord-5a69668bbdd94a21845f8b021fa41096
出典データセット
uspto-grants-1998_05
特許番号
US05750540

反応ノート

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