1-(6-Methoxypyridin-3-yl)-2-nitro-propan-1-ol → HCID 68479850, compound

HRID 1098785Notes

Reaction equation

HRID 1098785 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:15])[CH:10]([N+:12]([O-:14])=[O:13])[CH3:11])=[CH:5][CH:4]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:15])[CH:10]([N+:12]([O-:14])=[O:13])[CH3:11])=[CH:5][CH:4]=1.[NH2:12][C@@H:10]([CH3:11])[C@@H:9]([C:6]1[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[OH:15]

Participants

5

Reactant 2

HCID 593397011-(6-Methoxypyridin-3-yl)-2-nitro-propan-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 68479850HCID 68479850, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(6-methoxypyridin-3-yl)-2-nitro-propan-1-ol (17c) (2.20 g, 10.37 mmol) was dissolved in methanol (410 mL) and hydrogenated using a H-Cube™ hydrogenation reactor (THALES nanotechnology) equipped with a cartridge of 10% Pd/C. The flow rate was set to 0.8 mL/min, temperature 80° C. and full the hydrogen production at full mode. After evaporation of the solution diastereomers were separated on preparative HPLC (XTerrra C18, 19×50 mm) using a gradient of 5-30% acetonitrile in water (+1% NH3) gave the subtitle compound 17b (448 mg, 24%).

Workup

  1. customwas set to 0.8 mL/min, temperature 80° C.
  2. customAfter evaporation of the solution diastereomers
  3. customwere separated on preparative HPLC (XTerrra C18, 19×50 mm)

Sources & evidence

ORD record
ord-d53b599c275146fe9222d221ec9a230e
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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