Ethanol → 5-Allyl-6a-(2-fluorophenyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole

HRID 338086

反応式

HRID 338086 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11])=O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.[NH2:19]O.[CH2:21]([OH:23])C>>[CH2:17]([N:12]1[CH2:13][CH:14]2[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[F:11])([NH:19][O:23][CH2:21]2)[CH2:2]1)[CH:16]=[CH2:15]

参加物

5

反応物 4

HCID 702Ethanol2 回HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 27374492-Bromo-2'-fluoroacetophenone

生成物 1

HCID 866978985-Allyl-6a-(2-fluorophenyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole収率 58%

実験手順

To a solution of 2-bromo-1-(2-fluorophenyl)ethanone (10.0 g, 46.1 mmol) in ethanol (460.8 mL) is added drop wise diallyamine (9.4 g, 96.8 mmol) in ethanol (460.8 mL). The reaction is stirred for 2 hr. Pyridine is then added to the reaction (11.2 mL, 138.2 mmol) followed by the addition of hydroxylamine hydrochloride (4.8 g, 69.1 mmol). The reaction is refluxed for 4 hr and then concentrated to dryness. The residue is dissolved in toluene (230.4 mL) and is refluxed for 8 hr. The mixture is cooled to room temperature and extracted with saturated sodium bicarbonate solution. The aqueous phase is then extracted with DCM. The organic phase is concentrated and the mixture purified by silica gel chromatography eluting with hexane to 1:1 hexane/ethyl acetate to give the title compound (6.6 g, 58%). ES/MS (m/e): 248 (M+H).

後処理

  1. temperatureThe reaction is refluxed for 4 hr
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue is dissolved in toluene (230.4 mL)
  4. temperatureis refluxed for 8 hr
  5. extractionextracted with saturated sodium bicarbonate solution
  6. extractionThe aqueous phase is then extracted with DCM
  7. concentrationThe organic phase is concentrated
  8. customthe mixture purified by silica gel chromatography
  9. washeluting with hexane to 1:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-1ea8249382284ce0b897ac968550fdba
出典データセット
uspto-grants-2014_11
特許番号
US08889856B2

関連ノート

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