Water → HCID 20821664, compound

HRID 584782Notes

Reaction equation

HRID 584782 reaction equation
C(OC([N:11]1[CH2:16][C@@H:15]([OH:17])[C@H:14]([OH:18])[C@@H:13]([OH:19])[C@H:12]1[C:20]([OH:22])=[O:21])=O)C1C=CC=CC=1.[H][H].O>CO.[Pd].O.CO>[OH:19][C@@H:13]1[C@@H:14]([OH:18])[C@H:15]([OH:17])[CH2:16][NH:11][C@@H:12]1[C:20]([OH:22])=[O:21]

Participants

7

Reactant 3

HCID 962WaterHCID 69732539HCID 69732539, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20821664HCID 20821664, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

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);

Workup

  1. filtrationCatalyst was filtered through celite pad and volatiles
  2. customwere removed
  3. customPure product was isolated by flash chromatography on silicagel

Sources & evidence

ORD record
ord-7ab1a02e439c458db693e111e266a640
Source dataset
uspto-grants-2005_08
Patent number
US06927294B1

Reaction notes

Loading…