Cesium carbonate → Tert-butyl 4-[4-(trifluoromethoxy)phenyl]piperazine-1-carboxylate

HRID 32705

反応式

HRID 32705 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:53]([O:57][C:58]([N:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1)=[O:59])([CH3:56])([CH3:55])[CH3:54].Br[C:67]1[CH:72]=[CH:71][C:70]([O:73][C:74]([F:77])([F:76])[F:75])=[CH:69][CH:68]=1>C(OC(=O)C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:53]([O:57][C:58]([N:60]1[CH2:65][CH2:64][N:63]([C:67]2[CH:68]=[CH:69][C:70]([O:73][C:74]([F:75])([F:76])[F:77])=[CH:71][CH:72]=2)[CH2:62][CH2:61]1)=[O:59])([CH3:56])([CH3:54])[CH3:55]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 634876Binap, (A+-)-

生成物 1

HCID 59793537Tert-butyl 4-[4-(trifluoromethoxy)phenyl]piperazine-1-carboxylate収率 13%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a mixture of cesium carbonate (1.88 g, 5.7 mmol), palladium(II)acetate (46.1 mg, 0.205 mmol), rac-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (192 mg, 0.31 mmol), tert-Butyl-1-piperazine carboxylate (928 mg, 4.93 mmol) and 1-Bromo-4-(trifluoromethoxy)benzene (1 g, 4.11 mmol) was added degazed toluene (10 ml). The mixture was heated to 100° C. for 4 hours. The mixture was cool to room temperature, diluted with ethylacetate, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over silica gel: eluent: heptane/ethylacetate 0-10% over 20 minutes to provide the title compound (180 mg, 13%) as a yellow solid, MS (m/e): 347.4 (M+H, 100%).

後処理

  1. temperatureThe mixture was cool to room temperature
  2. filtrationfiltered
  3. customthe solvent was removed in vacuo
  4. customThe crude oil was chromatographed over silica gel

出典と根拠

ORDレコード
ord-b45b3fee9e4a4e5f8550d6537c6cfb9b
出典データセット
uspto-grants-2008_09
特許番号
US07427612B2

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