3-(3-Benzyloxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester → 3-(3-Hydroxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

HRID 852638Notes

Reaction equation

HRID 852638 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([O:16][CH2:17][CH2:18][CH2:19][O:20]CC2C=CC=CC=2)[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([O:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:5]=1

Participants

4

Reactant 1

HCID 693568053-(3-Benzyloxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

Product 1

HCID 693569733-(3-Hydroxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl esterYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

3-(3-Benzyloxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D38) in MeOH (15 ml) was hydrogenolysed initially with 10% Pd on charcoal (50% wet, 0.25 g, 0.25 equiv w/w) at atmospheric pressure for 24 hrs and then a further 0.25 g of 10% Pd on charcoal (50% wet, 0.25 g, 0.25 equiv w/w) was added and the mixture hydrogenolysed at 50 psi for a further 48 hrs. The mixture was filtered through Celite and concentrated in vacuo. Purification by flash chromatography on silica gel (AcOEt/iso-hexane: 1/1) gave 3-(3-hydroxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B15) (260 mg, 69% over 2 steps). [M+H]+=294.0

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customPurification by flash chromatography on silica gel (AcOEt/iso-hexane: 1/1)

Sources & evidence

ORD record
ord-43765deb14744d2bade5ed1d9ad97690
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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