HCID 57827207, compound → HCID 57827514, compound

HRID 1842273Notes

Reaction equation

HRID 1842273 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-5d5b9a3473b74f5b8e100cddbc0e30d5
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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