Water → t-Butyl 4-(4-trifluoromethylsulfonylphenoxy)piperidine-1-carboxylate

HRID 1792507

反応式

HRID 1792507 の反応式
I([O-])(=O)(=O)=O.[Na+].[F:7][C:8]([S:11][C:12]1[CH:31]=[CH:30][C:15]([O:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[CH:14][CH:13]=1)([F:10])[F:9].C(=O)(O)[O-:33].[Na+].[OH2:37]>O.[Ru](Cl)(Cl)Cl>[F:9][C:8]([F:7])([F:10])[S:11]([C:12]1[CH:31]=[CH:30][C:15]([O:16][CH:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:21][CH2:22]2)=[CH:14][CH:13]=1)(=[O:33])=[O:37]

参加物

6

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 22031376t-Butyl 4-(4-trifluoromethylsulfanyl-phenoxy)piperidine-1-carboxylateHCID 23667635Sodium periodate

生成物 1

HCID 22031673t-Butyl 4-(4-trifluoromethylsulfonylphenoxy)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6093376Ruthenium trichloride hydrate触媒

実験手順

2.55 g sodium periodate and 0.4 mg ruthenium (III) chloride hydrate were added to 60 mL solution mixture (carbon tetrachloride/acetonitrile/water=1:1:2) of 1.5 g t-butyl 4-(4-trifluoromethylsulfanyl-phenoxy)piperidine-1-carboxylate (compound in Production Example 454) with stirring under ice-cooling, and the mixture was stirred at room temperature for 1 hour. Water and a sodium bicarbonate solution were added thereto, and the reaction solution was extracted with ethyl acetate, dried over sodium sulfate and purified by silica gel chromatography (hexane/ethyl acetate) to give 1.3 g t-butyl 4-(4-trifluoromethylsulfonylphenoxy)piperidine-1-carboxylate. 2 mL solution of 4 N hydrogen chloride in ethyl acetate was added thereto and left for 1 hour. The solvent was removed, and the precipitated crystals were washed with ethyl acetate/ether to give 965 mg of the title compound as colorless crystals.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. custompurified by silica gel chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-7db1e17f438440e89fa606a0b0807925
出典データセット
uspto-grants-2006_07
特許番号
US07074801B1

関連ノート

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