(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 217995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217995
[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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 59281210[(2R,4R,5S)-5-amino-2-benzyloxymethyl-5-(5-bromo-2-fluorophenyl)tetrahydropyran-4-yl]methanolAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9f429fb9f5054911adb48b0c7b3452ce
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198269B2

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