(Z)-Prop-1-en-1-ylboronic acid → cis-2-benzyl-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole

HRID 1026629

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HRID 1026629 반응식
[CH2:1]([N:8]1[CH2:16][C@H:15]2[C@:10]([CH3:22])([CH2:11][CH2:12][C:13]3[C:20](Br)=[CH:19][CH:18]=[CH:17][C:14]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:23](/B(O)O)=[CH:24]/[CH3:25]>C([O-])([O-])=O.[Na+].[Na+].COCCOC.CCO>[CH2:1]([N:8]1[CH2:16][C@H:15]2[C@:10]([CH3:22])([CH2:11][CH2:12][C:13]3[C:20](/[CH:23]=[CH:24]\[CH3:25])=[CH:19][CH:18]=[CH:17][C:14]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 2

HCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 70664398cis-2-benzyl-6-bromo-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole

생성물 1

HCID 70664492cis-2-benzyl-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole

시약·촉매·용매 3

HCID 702Ethanol용매HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

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온도
160 °C

실험 절차

Tetrakis(triphenylphosphine)Pd(0) (0.021 mmol, 24.32 mg) was added in one portion to a mixture of cis-2-benzyl-6-bromo-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.421 mmol, 150 mg) and (Z)-prop-1-enylboronic acid (0.631 mmol, 54.2 mg) in 2 N aq Na2CO3 (1 ml), DME (1 ml) and EtOH (0.5 ml) The reaction mixture was heated under microwave irradiation at 160° C. for 900 seconds and then the mixture was filtered through celite. The resulting filtrate was diluted with water and extracted with DCM (3×). The combined organic extracts were dried over Na2SO4 and conc in vauco to afford a brown oil that was purified by silica column chromatography (eluting with 10% EtOAc in heptane) to afford cis-2-benzyl-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole) (127 mg), m/z: 318.3 [M+H]+.

후처리

  1. filtrationthe mixture was filtered through celite
  2. additionThe resulting filtrate was diluted with water
  3. extractionextracted with DCM (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4 and conc in vauco
  5. customto afford a brown oil that
  6. customwas purified by silica column chromatography (eluting with 10% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-8669a7ffe1e4458d8a10cb1235145559
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729274B2

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