HCID 59621263, compound → HCID 59621297, compound

HRID 1693222Notes

Reaction equation

HRID 1693222 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]12[CH2:16][CH2:15][CH:14]([O:17][CH3:18])[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])[CH2:16][CH2:15][CH:14]([O:17][CH3:18])[CH2:13][C@H:12]1[CH2:11][OH:10]

Participants

4

Reactant 1

HCID 59621263HCID 59621263, compound

Product 1

HCID 59621297HCID 59621297, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

(±)-(3aR*,7aS*)-7a-(2-Fluorophenyl)-5-methoxyoctahydrobenz[c]isoxazole obtained in Preparation Example 59-(5) (5.60 g) was dissolved in acetic acid (128 mL). Then, zinc powder (14.1 g) was added and the mixture was stirred at room temperature for eight hours. The solid was removed by filtration through celite, and then the celite was washed with ethyl acetate. The resulting filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate. Then, a saturated sodium bicarbonate solution was added, followed by vigorous stirring. The organic layer was separated and then the aqueous layer was extracted again with ethyl acetate twice. The combined organic layers were dried over anhydrous magnesium sulfate. The solid was removed by filtration and the filtrate was concentrated under reduced pressure to obtain the title compound (5.49 g).

Workup

  1. customThe solid was removed by filtration through celite
  2. washthe celite was washed with ethyl acetate
  3. concentrationThe resulting filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. additionThen, a saturated sodium bicarbonate solution was added
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted again with ethyl acetate twice
  8. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  9. customThe solid was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f558d120e47b45f6a2d8ac5c3ab8bd3d
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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