Trimethylsilylacetylene → (4-Tert-butyl-benzyl)-[2-(3-trimethylsilanylethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 19795ノート

反応式

HRID 19795 の反応式
[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23](Br)[CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31]>C(N(CC)CC)C.C([O-])(O)=O.[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=1)[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:34]#[C:33][Si:30]([CH3:32])([CH3:31])[CH3:29])[CH:22]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 68562789HCID 68562789、化合物

生成物 1

HCID 68560300(4-Tert-butyl-benzyl)-[2-(3-trimethylsilanylethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester収率 82.4%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8471Triethylamine溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
105 °C

実験手順

A mixture of the crude [2-(3-bromo-phenyl)-ethyl]-(4-tert-butyl-benzyl)-carbamic acid tert-butyl ester (515 mg, 1.154 mmol), bis(triphenylphosphine)palladium(II)chloride (32 mg, 0.0461 mmol), CuI (11 mg, 0.0577 mmol) and (trimethylsilyl)acetylene (251 μl, 1.73 mmol) in triethylamine (3.4 ml) was heated in a sealed tube at 105° C. over night. The mixture was then cooled to RT, diluted with sat. NaHCO3-solution and extracted three times with ethyl acetate. The combined ethyl acetate layers were then washed with water and brine and were dried (Na2SO4) and evaporated. The remaining residue was purified by chromatography (heptane/EtOAc 100:0 to 95:5) to obtain the title compound as a yellow gum (441 mg, 82%). MS (ISP) 464.4 (M+H)+.

後処理

  1. temperatureThe mixture was then cooled to RT
  2. extractionextracted three times with ethyl acetate
  3. washThe combined ethyl acetate layers were then washed with water and brine
  4. dry with materialwere dried (Na2SO4)
  5. customevaporated
  6. customThe remaining residue was purified by chromatography (heptane/EtOAc 100:0 to 95:5)

出典と根拠

ORDレコード
ord-8c4a07f24aa3494b88f1f616f709d796
出典データセット
uspto-grants-2010_06
特許番号
US07745477B2

反応ノート

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