HCID 59339701, compound → 2-Amino-1-[6-methoxypyridin-3-yl]propan-1-ol

HRID 1661478Notes

Reaction equation

HRID 1661478 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:15])[CH:10]([N+:12]([O-])=O)[CH3:11])=[CH:5][CH:4]=1.[H][H]>CO.[Pd]>[NH2:12][CH:10]([CH3:11])[CH: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 59339701HCID 59339701, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 597865832-Amino-1-[6-methoxypyridin-3-yl]propan-1-olYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(6-methoxypyridin-3-yl)-2-nitro-propan-1-ol (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 can be separated on preparative HPLC (XTerrra C18, 19×50 mm) using a gradient of 5-30% acetonitrile in water (+1% NH3) gave the pure subtitle compound (448 mg, 24%).

Workup

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

Sources & evidence

ORD record
ord-c3b9268e9efb4644b51ba3aa7a13f46e
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

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