Cesium carbonate → 1-(3-Phenylsulfonylphenyl)-4-tert-butyloxycarbonylpiperazine

HRID 855513ノート

反応式

HRID 855513 の反応式
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(=O)([O-])[O-].[Cs+].[Cs+].[C:53]1([S:59]([C:62]2[CH:63]=[C:64](Br)[CH:65]=[CH:66][CH:67]=2)(=[O:61])=[O:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.[C:69]([O:73][C:74]([N:76]1[CH2:81][CH2:80][NH:79][CH2:78][CH2:77]1)=[O:75])([CH3:72])([CH3:71])[CH3:70]>O1CCOCC1>[C:53]1([S:59]([C:62]2[CH:63]=[C:64]([N:79]3[CH2:78][CH2:77][N:76]([C:74]([O:73][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:75])[CH2:81][CH2:80]3)[CH:65]=[CH:66][CH:67]=2)(=[O:61])=[O:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 640920Benzene, 1-bromo-3-(phenylsulfonyl)-

生成物 1

HCID 688047411-(3-Phenylsulfonylphenyl)-4-tert-butyloxycarbonylpiperazine収率 71.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A solution of 2 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (62 mg, 0.1 mmol) and cesium carbonate (329 mg, 1.01 mmol) in dry dioxane (2 ml) were sonicated for 45 min, under argon. To this solution was added 3-phenylsulfonylbromobenzene (D2) (200 mg, 0.67 mmol) and 1-(tert-butyloxycarbonyl)piperazine (314 mg, 1.68 mmol) and the reaction heated at 100° C. for 18 h. The reaction mixture was evaporated in vacuo and the residue partitioned between water (50 ml) and dichloromethane (50 ml). The organic layer was washed with sat. sodium hydrogen carbonate (50 ml), 10% citric acid (50 ml), brine (50 ml) and then dried (MgSO4). Solvents evaporated in vacuo and the residue purified by column chromatography (silica gel; 0-60% ethyl acetate/petroleum ether) to give the product as a colourless oil (192 mg, 71%)

後処理

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue partitioned between water (50 ml) and dichloromethane (50 ml)
  3. washThe organic layer was washed with sat. sodium hydrogen carbonate (50 ml), 10% citric acid (50 ml), brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. customSolvents evaporated in vacuo
  6. customthe residue purified by column chromatography (silica gel; 0-60% ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-ddeb902ce7a64ae688d3c01c150e46fa
出典データセット
uspto-grants-2007_08
特許番号
US07262188B2

反応ノート

読み込み中…