HCID 57827207, compound → HCID 57827514, compound

HRID 1693245Notes

Reaction equation

HRID 1693245 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@:7]23[CH2:15][CH2:14][O:13][CH2:12][C@H:11]2[CH2:10][O:9][NH:8]3)[S:5][CH:6]=1>C(O)(=O)C.[Zn]>[NH2:8][C@@:7]1([C:4]2[S:5][CH:6]=[C:2]([Br:1])[CH:3]=2)[CH2:15][CH2:14][O:13][CH2:12][C@H:11]1[CH2:10][OH:9]

Participants

4

Reactant 1

HCID 57827207HCID 57827207, compound

Product 1

HCID 57827514HCID 57827514, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc (374 mg) was added to a solution of (±)-(3aS*,7aS*)-7a-(4-bromo-thiophen-2-yl)-hexahydro-pyrano[4,3-c]isoxazole (166 mg) in acetic acid (5 mL), and the mixture was stirred at room temperature overnight. The insoluble matter was removed by filtration through celite, and the solvent was evaporated under reduced pressure. Ice was added to the residue, followed by neutralization with a 2 N sodium hydroxide solution. The aqueous layer was extracted with ethyl acetate, 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 (147 mg).

Workup

  1. customThe insoluble matter was removed by filtration through celite
  2. customthe solvent was evaporated under reduced pressure
  3. additionIce was added to the residue
  4. extractionThe aqueous layer was extracted with ethyl acetate
  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

Sources & evidence

ORD record
ord-d1af122d962d47a582257599f3e9c8f2
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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