Water → HCID 20821664, compound

Participants

Reaction Steps

To the solution of 2S,3S,4S,5R)-N-Benzyloxycarbonyl-3,4,5-trihydroxypiperidine-2-carboxylic acid (Example 40) (41.7 mg, 0.14 mmol) in MeOH (4 mL) was added Pd/C catalyst (5% wt, 60 mg). The reaction mixture was stirred under the atmosphere of hydrogen gas for 6 h. Catalyst was filtered through celite pad and volatiles were removed. Pure product was isolated by flash chromatography on silicagel using H2O-MeOH (2:98) as an eluent (16.7 mg, 72% yield). [α]D=−8.6° (C=0.21, H2O). 1H NMR (360 MHz, D2O+ two drops of MeOD-d4) δ 4.09-4.00 (m, 1H), 3.89-3.75 (m, 3H), 3.23 (dd, J=13.1, 1.9 Hz, 1H), 3.08 (dd, J=13.1, 3.8 Hz, 1H);

Provenance & Evidence