HCID 66750331, compound → HCID 59541792, compound

HRID 2388323Notes

Reaction equation

HRID 2388323 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:12]=[CH:13][C:14](=[O:17])[NH:15][CH:16]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H][H]>C(OCC)(=O)C.[Pd]>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[CH:12]=[CH:13][C:14](=[O:17])[NH:15][CH:16]=3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 66750331HCID 66750331, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59541792HCID 59541792, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-1H-pyridin-2-one from Step A of Example 37 (5.2 g, 22.1 mmol) in ethyl acetate (30 mL) was treated with 5% Pd/C (Aldrich, 2.6 g) at room temperature. The reaction mixture was then charged with a hydrogen balloon and stirred for 2 hours. The catalyst was removed by filtering the reaction through a pad of Celite. The filtrate was concentrated to give the crude product, which was then purified with a CombiFlash® system using silica gel column and 40% ethyl acetate in hexanes as eluent to give the title compound as a white solid.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering
  3. customthe reaction through a pad of Celite
  4. concentrationThe filtrate was concentrated
  5. customto give the crude product, which
  6. customwas then purified with a CombiFlash® system

Sources & evidence

ORD record
ord-da9abf7bdcec40c1b25d7b0b9965802a
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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