Tris(propan-2-yl)silanethiol → 4-(2-Triisopropylsilanylsulfanyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2244042

반응식

HRID 2244042 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2OS(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:37]([Si:40]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[SH:41])([CH3:39])[CH3:38].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:41][Si:40]([CH:42]([CH3:44])[CH3:43])([CH:45]([CH3:47])[CH3:46])[CH:37]([CH3:38])[CH3:39])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

참가 물질

6

반응물 3

HCID 3435097Tris(propan-2-yl)silanethiolHCID 23676156Sodium t-butoxideHCID 866181014-[2-(Nonafluorobutane-1-sulfonyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 686357834-(2-Triisopropylsilanylsulfanyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester수율 45.2%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

Bis[(2-diphenylphosphino)phenyl]ether (0.43 g; 0.80 mmol) and tris(dibenzylideneacetone)-dipalladium (0.37 mg; 0.40 mmol) were dissolved in 40 mL toluene. 4-[2-(Nonafluorobutane-1-sulfonyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (4.34 g; 7.76 mmol), triisopropyl-silanethiol (1.83 mL; 8.53 mmol) and sodium tert-butoxide (0.90 g; 9.3 mmol) were added and the reaction mixture was stirred under argon for 3 hours at 100° C. The reaction mixture was cooled to room temperature filtered through a pad of silica and concentrated in vacuo. The residue was purified by flash chromatography (silica gel; ethyl acetate/heptane) to give 1.58 g 4-(2-triisopropylsilanylsulfanyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (3.51 mmol; 45%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a pad of silica
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (silica gel; ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-2901406dc23346ca8309fc82d596b1fd
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678800B2

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