Tri-o-tolylphosphine → 4-(3'-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 25858

反応式

HRID 25858 の反応式
CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CC([O-])(C)C.[Na+].[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][NH:39][C@@H:38]([CH:42]([CH3:44])[CH3:43])[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].[CH2:45]([C:52]1[CH:57]=[CH:56][CH:55]=[C:54](Br)[CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>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(Cl)Cl.CO>[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([C:54]2[CH:55]=[CH:56][CH:57]=[C:52]([CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH:53]=2)[C@@H:38]([CH:42]([CH3:44])[CH3:43])[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]

参加物

8

反応物 4

HCID 80271Tri-o-tolylphosphineHCID 5975321-Benzyl-3-bromobenzeneHCID 23676156Sodium t-butoxideHCID 24820348(S)-1-Boc-3-isopropylpiperazine

生成物 1

HCID 691298694-(3'-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester収率 22.71%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
100 °C

実験手順

17.9 mg (19.55 μmol, 0.044 eq.) Pd2(dba)3 and 5.9 mg (19.38 μmol, 0.044 eq.) P(o-tolyl)3 were dissolved in 6 ml dry toluene. Then 58.9 mg (610 μmol, 1.39 eq.) NaOt-Bu was added, followed by a solution of 101 mg (442 μmol) 3-(S)-Isopropyl-piperazine-1-carboxylic acid tert-butyl ester (85) and 110 mg (445 μmol, 1.01 eq.) 1-Benzyl-3-bromo-benzene (87). The resulting mixture was heated at 100° C. for 19 h. After filtrating the reaction mixture through celite the solvent was evaporated. Column chromatography (hexanes/EtOAc (3+1)) yielded 39.6 mg (100 μmol, 22.71%) 4-(3′-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester (88).

後処理

  1. filtrationAfter filtrating the reaction mixture through celite the solvent
  2. customwas evaporated

出典と根拠

ORDレコード
ord-356d45150e6647dbaba90ac148ea6498
出典データセット
uspto-grants-2005_02
特許番号
US06858600B2

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