Ethanolamine → 2-(((2-(Benzyloxy)-4,6-dimethylpyridin-3-yl)methyl)amino)ethanol

HRID 577464Notes

Reaction equation

HRID 577464 reaction equation
[CH2:1]([O:8][C:9]1[N:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][OH:22].C([BH3-])#N.[Na+]>CO>[CH2:1]([O:8][C:9]1[C:10]([CH2:11][NH:19][CH2:20][CH2:21][OH:22])=[C:13]([CH3:18])[CH:14]=[C:15]([CH3:17])[N:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 5003444Sodium cyanoborohydrideHCID 229349822-(Benzyloxy)-4,6-dimethylnicotinaldehyde

Product 1

HCID 867236942-(((2-(Benzyloxy)-4,6-dimethylpyridin-3-yl)methyl)amino)ethanolYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-(benzyloxy)-4,6-dimethylnicotinaldehyde (Cpd JJ, 6.4 g, 27 mmol) in methanol (100 mL) was added 2-aminoethanol (8.34 mL, 133 mmol). The reaction mixture was stirred at room temperature for 1 hour then cooled to 0° C. Sodium cyanoborohydride (4.9 g, 66 mmol) was added in one portion and the reaction was slowly warmed to room temperature and stirred overnight. The methanol was removed under vacuum then the residue was diluted with water (50 mL) and extracted with dichloromethane (2×50 mL). The combined organic extracts were dried over magnesium sulfate, concentrated under vacuum and purified by column chromatography (EtOAc) to give 2-(((2-(benzyloxy)-4,6-dimethylpyridin-3-yl)methyl)amino)-ethanol (Cpd KK, 4.2 g, 55% yield) as a pale yellow solid.

Workup

  1. temperaturethen cooled to 0° C
  2. temperaturethe reaction was slowly warmed to room temperature
  3. stirringstirred overnight
  4. customThe methanol was removed under vacuum
  5. additionthe residue was diluted with water (50 mL)
  6. extractionextracted with dichloromethane (2×50 mL)
  7. dry with materialThe combined organic extracts were dried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. custompurified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-aab7c2e459854465b6c4daccac7d35e1
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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