HCID 11708770, compound → 1-(4-hydroxyphenyl)pyrrolidin-2-one

HRID 1768130Notes

Reaction equation

HRID 1768130 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])=[CH:11][CH:10]=1)C1C=CC=CC=1.ClCCl.CO>C1COCC1.C(O)(=O)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 11708770HCID 11708770, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 7855861-(4-hydroxyphenyl)pyrrolidin-2-oneYield 66.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6.2 g (23.2 mmol) 1-(4-benzyloxy-phenyl)-pyrrolidin-2-one is dissolved in 200 ml THF. 3 drops of acetic acid are added and the solution is hydrogenated for 5 hours at RT and normal pressure in presence of 0.62 g palladium 10% on charcoal. Filtration and concentration gives a semisolid material. Chromatography (silica gel, dichloromethane/methanol 95:5) yields 2.73 g (66%) of a brownish solid. MS: m/e=175.9 (M−H).

Workup

  1. filtrationFiltration and concentration
  2. customgives a semisolid material

Sources & evidence

ORD record
ord-62365c17024d4fe0a584495a335ed946
Source dataset
uspto-grants-2007_06
Patent number
US07235581B2

Reaction notes

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