Reaction #171003

Reaction equation

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

→

62

Yield 62.8%

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

Yield 62.8%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration, and methanol
2. 2
   workup.DISTILLATIONdistilled off
3. 3
   OtherCrude 62 was purified by column chromatography on silica gel

Procedure

6-[4-(6-Benzyloxyhexanoylamino)-phenoxy]-hexanoic acid methyl ester 61 (10 g, 22.67 mmol) was dissolved in methanol (100 ml) in a pressure vessel. Palladium on carbon (5%, 6 grm) was added and the mixture stirred under a hydrogen atmosphere (4 kg) for 20 hrs. The catalyst was removed by filtration, and methanol distilled off. Crude 62 was purified by column chromatography on silica gel using chloroform as eluant to give pure 62 (5 g, 62.8%) as a white powder with a m.p. between 73-75.5° C.

Source