Potassium Carbonate → HCID 89854038, compound

HRID 931267Notes

Reaction equation

HRID 931267 reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N+:5]=1[O-:10].[CH2:11]([NH:18][C@@H:19]([CH3:22])[CH2:20][OH:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:11]([N:18]([C@@H:19]([CH3:22])[CH2:20][OH:21])[CH2:3][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N+:5]=1[O-:10])[OH:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3319172-(Oxiran-2-yl)-1-oxo-1lambda~5~-pyridineHCID 5356540(S)-2-(Benzylamino)propan-1-ol

Product 1

HCID 89854038HCID 89854038, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(oxiran-2-yl)pyridine 1-oxide (6.6 g, 48.48 mmol) in ethanol (150 mL) were added (S)-2-(benzylamino)propan-1-ol (16 g, 96.96 mmol) and potassium carbonate (13.3 g, 96.96 mmol), After 24 h, the mixture was concentrated under reduced pressure and the resulting residue was purified via alumina chromatography (1% methanol in dichloromethane) to afford 2-(2-(benzyl((S)-1-hydroxypropan-2-yl)amino)-1-hydroxyethyl)pyridine 1-oxide as a yellow liquid (7 g, 22%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified via alumina chromatography (1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f0579ccc7bcf40b0ab6c706424444064
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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