HCID 118511153, compound → HCID 118511071, compound

HRID 1478182Notes

Reaction equation

HRID 1478182 reaction equation
[CH3:1][C:2]1[C:3]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:4][O:5][C:6]=1[C:7]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH:8]=1>C(O)C.[Pd]>[CH3:1][C:2]1[C:3]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:4][O:5][C:6]=1[CH:7]1[CH2:8][CH2:9][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 118511153HCID 118511153, compound

Product 1

HCID 118511071HCID 118511071, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 4-methyl-5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)isoxazole-3-carboxylate (556 mg, 1.896 mmol) in ethanol (20 mL) was flushed with nitrogen and then treated with 10% Pd—C, 50% wet (Alfa Aesar, 38303) (303 mg, 2.84 mmol). The reaction mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The resulting mixture was filtered through Celite®, washing with ethanol and DCM. The filtrate was concentrated under reduced pressure and the residue was passed through a 500 mg silica-TMT cartridge, eluting with ethanol:ether (1:1). The solvent was removed under reduced pressure to afford the title compound;

Workup

  1. filtrationThe resulting mixture was filtered through Celite®
  2. washwashing with ethanol and DCM
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washeluting with ethanol:ether (1:1)
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ed96f21bf82b4377ace9d834ad0cf8b5
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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