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

HRID 971372

반응식

HRID 971372 반응식
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]

참가 물질

9

반응물 4

HCID 5975321-Benzyl-3-bromobenzeneHCID 21226129Dichloromethane methanolHCID 23676156Sodium t-butoxideHCID 24820348(S)-1-Boc-3-isopropylpiperazine

생성물 1

HCID 691298694-(3'-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester수율 59,322%

시약·촉매·용매 4

HCID 27349392'-(diphenylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3a84720c0602453bb5036f899a18eba6
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312246B2

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