(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
Reaction equation
[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]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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).
Workup
- customthe insoluble matter was removed by filtration through celite
- customThe solvent was evaporated under reduced pressure and ice
- additionwas added to the residue
- extractionThe aqueous layer was extracted with dichloromethane
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-9f429fb9f5054911adb48b0c7b3452ce
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198269B2
Reaction notes
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