D-Psicose → HCID 24267036, compound

HRID 717790Notes

Reaction equation

HRID 717790 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>C(O)C.[Pt]=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 11401811HCID 11401811, compound

Product 1

HCID 24267036HCID 24267036, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

3-(4-Fluorophenyl) quinoline (1 g, 0.00448 mol) was dissolved in ethanol (25 mL), and to this was added platinum oxide (0.4 g) under nitrogen atmosphere. The reaction mixture was hydrogenated at 45 Psi for 10 h. After completion of reaction (monitored by TLC), the catalyst was removed by filtration, and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography (silica 100-200 mesh, diameter of column—2.5 cm, height of silica—approx. 5 inch) to provide the desired compound (0.25 g, 25% yield).

Workup

  1. customAfter completion of reaction (monitored by TLC)
  2. customthe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe crude product was purified by column chromatography (silica 100-200 mesh, diameter of column—2.5 cm, height of silica—approx. 5 inch)

Sources & evidence

ORD record
ord-b820fe70f88c4c3c9be47085f2dc14ac
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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