Reaction #725938

Reaction equation

6-[4-(6-Benzyloxyhexanoylamino)phenoxy]hexanoic acid methyl ester

→

81

Yield 62.8%

6-[4-(6-Hydroxyhexanoylamino)phenoxy]hexanoic acid methyl ester

Yield 62.8%

Solvents

methanol

Conditions

Workup

1. 1
   OtherCatalyst was removed by filtration and methanol
2. 2
   workup.DISTILLATIONdistilled off
3. 3
   OtherCrude 81 was purified by column chromatography on silica gel

Procedure

6-[4-(6-Benzyloxyhexanoylamino)phenoxy]hexanoic acid methyl ester 80 (10 g, 22.67 mmol) was dissolved in methanol (100 ml) in a pressure vessel, palladium on carbon (5%, 6 grams) added, and the mixture stirred under a hydrogen atm. (4 Kg) for 20 hrs. Catalyst was removed by filtration and methanol distilled off. Crude 81 was purified by column chromatography on silica gel using chloroform as eluant to give pure 81 (5 g, 62.8%) as a white powder. M.p: 73-75.5°

Source