(3aR*,5R*,6aS*)-6a-(2-fluorophenyl)-5-methoxy-hexahydrocyclopenta[c]isoxazole → [(1R*,2S*,4R*)-2-amino-2-(2-fluorophenyl)-4-methoxycyclopentyl]methanol

HRID 1842196Notes

Reaction equation

HRID 1842196 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

Reactant 1

HCID 57827338(3aR*,5R*,6aS*)-6a-(2-fluorophenyl)-5-methoxy-hexahydrocyclopenta[c]isoxazole

Product 1

HCID 57827534[(1R*,2S*,4R*)-2-amino-2-(2-fluorophenyl)-4-methoxycyclopentyl]methanolYield 97.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Zinc (533 mg) was added to a solution of (3aR*,5R*,6aS*)-6a-(2-fluorophenyl)-5-methoxy-hexahydrocyclopenta[c]isoxazole (275 mg) in acetic acid (5.57 mL), and the mixture was stirred at room temperature for 12 hours. More 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 (270 mg).

Workup

  1. stirringby stirring at room temperature for three hours
  2. customZinc was removed by filtration
  3. additionthe filtrate was poured into a saturated sodium bicarbonate solution
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-87a96e6314bf49c191866463545ab27d
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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