8-Benzyl-6-hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one → 6-Hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1848477Notes

Reaction equation

HRID 1848477 reaction equation
C([N:8]1[CH2:25][CH2:24][C:11]2([C:15](=[O:16])[N:14]([C:17]3[CH2:18][O:19][C:20](=[O:23])[C:21]=3[CH3:22])[CH2:13][CH2:12]2)[CH:10]([OH:26])[CH2:9]1)C1C=CC=CC=1>CO.[Pd].CC(O)=O>[OH:26][CH:10]1[CH2:9][NH:8][CH2:25][CH2:24][C:11]21[C:15](=[O:16])[N:14]([C:17]1[CH2:18][O:19][C:20](=[O:23])[C:21]=1[CH3:22])[CH2:13][CH2:12]2

Participants

5

Reactant 1

HCID 867094878-Benzyl-6-hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 867094886-Hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-benzyl-6-hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (150 mg, 0.42 mmol) in MeOH (2 mL) was added palladium on carbon (45 mg, 0.42 mmol) and a few drops of HOAc. The mixture was allowed to stir under an atmosphere of hydrogen for 16 hours. LC indicated complete reaction. The catalyst was filtered off, and the crude material was used without further purification. LCMS: m/z 267 (M+H)+.

Workup

  1. customreaction
  2. filtrationThe catalyst was filtered off
  3. customthe crude material was used without further purification

Sources & evidence

ORD record
ord-b6172265c4844d399b58c56f47a5c94e
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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