Benzyl Alcohol → Benzyl 2-(4-(4'-amino-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881742노트

반응식

HRID 881742 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]34[CH2:21][CH2:20][C:17]([CH2:22][C:23]([O:25][CH3:26])=[O:24])([CH2:18][CH2:19]3)[O:16][CH2:15]4)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1.CCOC(C)=O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]34[CH2:19][CH2:18][C:17]([CH2:22][C:23]([O:25][CH2:26][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[O:24])([CH2:20][CH2:21]3)[O:16][CH2:15]4)=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 2

HCID 244Benzyl AlcoholHCID 86700832Methyl 2-(4-(4'-aminobiphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

생성물 1

HCID 86700844Benzyl 2-(4-(4'-amino-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate수율 68.8%

시약·촉매·용매 3

HCID 11026Titanium isopropoxide촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

To a mixture of methyl 2-(4-(4′-amino-[1,1′-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (0.323 g, 0.918 mmol) in toluene (35 ml) was added benzyl alcohol (2.377 ml, 22.95 mmol), titanium(IV) isopropoxide (0.807 ml, 2.75 mmol) and 4 A molecular sieves (5 g, 0.918 mmol). The reaction mixture was heated at 120° C. for 48 hours. The resulting mixture was taken up in EtOAc and filtered. The filtrate was subsequently washed with water, then brine. The organic portion dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (10 to 50% EtOAc/Heptane) to give the title compound after drying (270 mg, yield 68.8% yield). LC/MS, ESI-MS(+) m/z 428.1, RT 1.59 (Condition R).

후처리

  1. filtrationfiltered
  2. washThe filtrate was subsequently washed with water
  3. dry with materialThe organic portion dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (10 to 50% EtOAc/Heptane)

출처 및 근거

ORD 기록
ord-d3cd2d1fa35640c18b799d7adfdf72a4
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993619B2

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