2-Amino-1-butanol, (+)- → HCID 178456043, compound

HRID 899376Notes

Reaction equation

HRID 899376 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][N+:3]=1[O-:12].[NH2:13][C@@H:14]([CH2:17][CH3:18])[CH2:15][OH:16]>C(O)C>[OH:16][CH2:15][C@@H:14]([NH:13][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][N+:3]=1[O-:12])[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 1200842-Amino-1-butanol, (+)-HCID 123180102-Chloro-5-methyl-4-nitropyridine N-oxide

Product 1

HCID 178456043HCID 178456043, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-5-methyl-4-nitropyridine N-oxide (200 mg, 1.06 mmol, 1.0 equivalent) was dissolved in ethanol (1.5 mL). (S)-2-Aminobutanol (284 mg, 3.2 mmol, 3.0 equivalent) was then added and the resulting mixture was refluxed for 16 hours. The crude solution was then purified by reversed phase HPLC (acetonitrile/water/TFA) to afford the title compound as a brown solid (146 mg, 0.61 mmol, Rt(min) 3.787; FIA ES+ 241.8, ES− not observed).

Workup

  1. temperaturethe resulting mixture was refluxed for 16 hours
  2. customThe crude solution was then purified by reversed phase HPLC (acetonitrile/water/TFA)

Sources & evidence

ORD record
ord-9885a9374170465580a493429f8fbffd
Source dataset
uspto-grants-2008_04
Patent number
US07354939B2

Reaction notes

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