HCID 57121265, compound → HCID 15117379, compound

Participants

Reaction Steps

To a solution of 4-nitrobenzyl (5R,6S)-3-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (500 mg) in 0.1M phosphate buffer (pH 6.93, 20 ml) was added 20% (W/W) palladium on carbon (50% wet) and the solution was stirred under atmospheric pressure of hydrogen at ambient temperature for 5 hours. The catalyst was filtered off and the filtrate was concentrated in vacuo to give a residual solution, which was chromatographed on "Diaion HP-20" (100 ml) eluting in turn with water and a mixture of water and acetone (50:1-20:1, V/V). The fractions containing the desired compound were collected and lyophilized to give (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(piperidin-4-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (150 mg).

Provenance & Evidence