(3aR*,5S*,6aS*)-6a-(2-fluorophenyl)-5-methoxy-hexahydrocyclopenta[c]isoxazole → [(1R*,2S*,4S*)-2-amino-2-(2-fluorophenyl)-4-methoxycyclopentanyl]methanol
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]12[CH2:15][C@@H:14]([O:16][CH3:17])[CH2:13][C@H:12]1[CH2:11][O:10][NH:9]2>C(O)(=O)C.[Zn]>[NH2:9][C@@:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:15][C@@H:14]([O:16][CH3:17])[CH2:13][C@H:12]1[CH2:11][OH:10]Participants
4
Procedure
Zinc (533 mg) was added to a solution of (3aR*,5S*,6aS*)-6a-(2-fluorophenyl)-5-methoxy-hexahydrocyclopenta[c]isoxazole (247 mg) in acetic acid (5 mL), and the mixture was stirred at room temperature for 12 hours. Zinc (500 mg) was added to the reaction solution, followed by stirring at room temperature for three hours. Zinc was removed by filtration and the filtrate was poured into a saturated sodium bicarbonate solution, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain the title compound (245 mg).
Workup
- stirringby stirring at room temperature for three hours
- customZinc was removed by filtration
- additionthe filtrate was poured into a saturated sodium bicarbonate solution
- extractionfollowed by extraction with ethyl acetate
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- customThe drying agent was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2589334d9da44b9aa25a229aaf76ffde
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946210B2
Reaction notes
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