Tetrahydrofuran → (+/-)-(3aR*,7aS*)-7a-(2,2-difluorobenzo[1,3]dioxol-4-yl)hexahydropyrano[3,4-c]isoxazole

HRID 218002ノート

反応式

HRID 218002 の反応式
C1COCC1.Br[C:7]1[C:15]2[O:14][C:13]([F:17])([F:16])[O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.[N:18]1[O:19][CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][C:22]=12.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.C1COCC1>[F:16][C:13]1([F:17])[O:12][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C@:22]34[CH2:23][O:24][CH2:25][CH2:26][C@H:21]3[CH2:20][O:19][NH:18]4)[C:15]=2[O:14]1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 27732974-Bromo-2,2-difluoro-1,3-benzodioxoleHCID 574756753,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazole

生成物 1

HCID 59281184(+/-)-(3aR*,7aS*)-7a-(2,2-difluorobenzo[1,3]dioxol-4-yl)hexahydropyrano[3,4-c]isoxazole

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 22635083Tetrahydrofuran toluene溶媒

反応条件

温度
-78 °C

実験手順

THF (2.0 ml) was added to a solution of 4-bromo-2,2-difluoro-1,3-benzodioxol (1.96 g) in toluene (20 ml). The mixture was cooled to −78° C., and a solution of (±)-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazole obtained in Preparation Example 1-(2) (500 mg) in toluene-THF (10:1) (10 ml) and a boron trifluoride-diethyl ether complex (990 μl) were added dropwise at the same time. After stirring at the same temperature for two hours, an ammonium chloride solution was added to terminate the reaction. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (873 mg).

後処理

  1. additiona boron trifluoride-diethyl ether complex (990 μl) were added dropwise at the same time
  2. customto terminate
  3. customthe reaction
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-31e5add7439042dbb9cab2f889fb90f9
出典データセット
uspto-grants-2012_06
特許番号
US08198269B2

反応ノート

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