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

Participants

Reaction Steps

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

Provenance & Evidence