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Tetrahydrofuran → 3-(2-Benzyloxy-3-cyanophenyl)-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

HRID 2403975
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HRID 2403975 반응식
[CH2:1]([O:8][C:9]1[C:16](Br)=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([O:22][C:23]([N:25]1[CH:30]2[CH2:31][CH2:32][CH:26]1[CH:27]=[C:28](B1OC(C)(C)C(C)(C)O1)[CH2:29]2)=[O:24])([CH3:21])([CH3:20])[CH3:19].C1COCC1.C(=O)([O-])[O-].[Na+].[Na+]>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:18]([O:22][C:23]([N:25]1[CH:30]2[CH2:31][CH2:32][CH:26]1[CH:27]=[C:28]([C:16]1[CH:15]=[CH:14][CH:13]=[C:10]([C:11]#[N:12])[C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:29]2)=[O:24])([CH3:21])([CH3:19])[CH3:20]
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참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 53393373Tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo(3.2.1)oct-2-ene-8-carboxylateHCID 598089582-(Benzyloxy)-3-bromobenzonitrile

생성물 1

HCID 671520573-(2-Benzyloxy-3-cyanophenyl)-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester수율 64.5%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

실험 절차

To a flask was added 2-benzyloxy-3-bromobenzonitrile (1.29 g, 4.47 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester (1.50 g, 4.47 mmol), and THF (30 mL), 2.0 M sodium carbonate in water (8.95 mL), and bis(triphenylphosphine)palladium(II) chloride (78 mg, 0.11 mmol). The reaction mixture was purged with nitrogen, heated to reflux overnight, cooled to room temperature, and concentrated. The resulting solution was diluted with DCM (25 mL) and washed with water (25 mL) The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by flash column chromatraphy eluting with ethyl acetate in hexanes (0-50%) to give partially purified product (1.2 g). (m/z): [M+H]+ calcd for C26H28N2O3 416.21; (-tert-butyl 361.2). found 361; (-Boc 317.2). found 317.

후처리

  1. customThe reaction mixture was purged with nitrogen
  2. temperatureheated
  3. temperatureto reflux overnight
  4. concentrationconcentrated
  5. additionThe resulting solution was diluted with DCM (25 mL)
  6. washwashed with water (25 mL) The organic layer
  7. customwas collected
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by flash column chromatraphy
  12. washeluting with ethyl acetate in hexanes (0-50%)

출처 및 근거

ORD 기록
ord-2e022e31b16445cbb5c09588208d82e7
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08802698B2

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