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2,4-Dibromo-1-fluorobenzene → (+/-)-(3aR*,7aS*)-7a-(5-bromo-2-fluorophenyl)-hexahydropyrano[3,4-c]isoxazole

HRID 217998
ノート
印刷プレビュー

反応式

HRID 217998 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4](Br)[CH:3]=1.C([Li])CCC.[N:15]1[O:16][CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][C:19]=12>C1(C)C=CC=CC=1.C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([C@:19]23[CH2:20][O:21][CH2:22][CH2:23][C@H:18]2[CH2:17][O:16][NH:15]3)[CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 150342,4-Dibromo-1-fluorobenzeneHCID 574756753,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazoleHCID 178418339Butyllithium

生成物 1

HCID 59281218(+/-)-(3aR*,7aS*)-7a-(5-bromo-2-fluorophenyl)-hexahydropyrano[3,4-c]isoxazole

試薬・触媒・溶媒 1

HCID 22635083Tetrahydrofuran toluene溶媒2 回

反応条件

温度
-78 °C

実験手順

1,3-Dibromo-4-fluorobenzene (837 mg) was dissolved in a toluene-THF (10:1) mixture (15 ml). The mixture was cooled to −78° C. and n-butyllithium (2.64 M, 1.19 ml) was added dropwise. After stirring at the same temperature for one hour, a solution of (±)-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazole obtained in Preparation Example 1-(2) (200 mg) in toluene-THF (10:1) (5.0 ml) and a boron trifluoride-diethyl ether complex (394 μl) were added dropwise at the same time. After stirring at the same temperature for three hours, the reaction was terminated with an ammonium chloride solution. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (365 mg).

後処理

  1. additiona boron trifluoride-diethyl ether complex (394 μl) were added dropwise at the same time
  2. stirringAfter stirring at the same temperature for three hours
  3. customthe reaction was terminated with an ammonium chloride solution
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe organic layer was washed with water and brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-1d6841f74bc844ed9f0bc8cc83fddfb0
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08198269B2

反応ノート

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