(3aR,5R,7aS)-5-benzyloxymethyl-7a-(5-bromo-2-fluorophenyl)hexahydropyrano[3,4-c]isoxazole → [(2R,4R,5S)-5-amino-2-benzyloxymethyl-5-(5-bromo-2-fluorophenyl)tetrahydropyran-4-yl]methanol

HRID 217995노트

반응식

HRID 217995 반응식
[CH2:1]([O:8][CH2:9][C@@H:10]1[O:18][CH2:17][C@:13]2([C:19]3[CH:24]=[C:23]([Br:25])[CH:22]=[CH:21][C:20]=3[F:26])[NH:14][O:15][CH2:16][C@@H:12]2[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[NH2:14][C@@:13]1([C:19]2[CH:24]=[C:23]([Br:25])[CH:22]=[CH:21][C:20]=2[F:26])[CH2:17][O:18][C@@H:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:11][C@H:12]1[CH2:16][OH:15]

참가 물질

4

반응물 1

HCID 59281209(3aR,5R,7aS)-5-benzyloxymethyl-7a-(5-bromo-2-fluorophenyl)hexahydropyrano[3,4-c]isoxazole

생성물 1

HCID 59281210[(2R,4R,5S)-5-amino-2-benzyloxymethyl-5-(5-bromo-2-fluorophenyl)tetrahydropyran-4-yl]methanol수율 80.6%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

실험 절차

Zinc powder (4.24 g) was added to a solution of (3aR,5R,7aS)-5-benzyloxymethyl-7a-(5-bromo-2-fluorophenyl)hexahydropyrano[3,4-c]isoxazole (2.74 g) in acetic acid (40 ml). After stirring at room temperature overnight, the insoluble matter was removed by filtration through celite. The solvent was evaporated under reduced pressure and ice was added to the residue, followed by neutralization with a 5 N sodium hydroxide solution. The aqueous layer was extracted with dichloromethane, 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 (2.22 g).

후처리

  1. customthe insoluble matter was removed by filtration through celite
  2. customThe solvent was evaporated under reduced pressure and ice
  3. additionwas added to the residue
  4. extractionThe aqueous layer was extracted with dichloromethane
  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

출처 및 근거

ORD 기록
ord-9f429fb9f5054911adb48b0c7b3452ce
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198269B2

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