1-Benzyl-3-bromobenzene → 4-(3'-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 971372

反応式

HRID 971372 の反応式
CC([O-])(C)C.[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][NH:17][C@@H:16]([CH:20]([CH3:22])[CH3:21])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[CH2:23]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32](Br)[CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(Cl)Cl.CO>C1(C)C=CC=CC=1.CCOCC.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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)C=CC=CC=1>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:32]2[CH:33]=[CH:34][CH:35]=[C:30]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:31]=2)[C@@H:16]([CH:20]([CH3:22])[CH3:21])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

参加物

9

反応物 4

HCID 5975321-Benzyl-3-bromobenzeneHCID 21226129Dichloromethane methanolHCID 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 59,322%

試薬・触媒・溶媒 4

HCID 27349392'-(diphenylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

9.4 mg (10.3 μmol, 0.013 eq.) Pd2(dba)3 and 11.4 mg (29.9 μmol, 0.04 eq.) 2-Diphenylphosphino-2′-dimethylamino-biphenyl were dissolved in 6 ml dry toluene. Then 170.7 mg (1.78 mmol, 2.32 eq.) NaOt-Bu was added, followed by a solution of 175.0 mg (0.77 mmol) 3-(S)-Isopropyl-piperazine-1-carboxylic acid tert-butyl ester (85) and 290.6 mg (1.18 μmol, 1.54 eq.) 1-Benzyl-3-bromo-benzene (87). The resulting mixture was heated at 80° C. for 22 h. After cooling to room temperature the mixture was diluted with ether and washed with brine. The comb. org. fractions were dried over Na2SO4 and evaporated. Column chromatography (hexanes/EtOAc (3+1)) yielded 276.5 mg (0.70 mmol, 91.49%) 4-(3′-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester (88).

後処理

  1. temperatureAfter cooling to room temperature the mixture
  2. washwashed with brine
  3. dry with materialfractions were dried over Na2SO4
  4. customevaporated

出典と根拠

ORDレコード
ord-3a84720c0602453bb5036f899a18eba6
出典データセット
uspto-grants-2007_12
特許番号
US07312246B2

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