Tetrahydrofuran → 6-(Methylamino)-2-pyridylethanol

HRID 2416694Notes

Reaction equation

HRID 2416694 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:10](=O)[CH2:11][C:12]1[N:17]=[C:16]([NH:18][CH3:19])[CH:15]=[CH:14][CH:13]=1)C.C1C[O:24]CC1>>[CH3:19][NH:18][C:16]1[N:17]=[C:12]([CH:11]([OH:24])[CH3:10])[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 22507068Ethyl 2-(6-(methylamino)pyridin-2-yl)acetate

Product 1

HCID 223194656-(Methylamino)-2-pyridylethanol

Conditions

Temperature
0 °C

Procedure

To a mechanically stirred solution of LiAlH4 in THF (1.0 M, 20 mL, 20.4 mmol) was added dropwise a solution of ethyl-2-(methylamino)-6-pyridylacetate (0.38 g, 2 mmol) in THF (10 mL). After the addition was completed, the reaction mixture was warmed to 0° C. and quenched with 10% NaOH solution. The solids were removed by filtration, and the filtrate was concentrated in vacuum. The residue was dissolved in CH2Cl2 and the solution was dried (MgSO4) and concentrated. Reconcentration from toluene (3×) gave the title compound as a colorless oil: MS (ES) m/e 153 (M+H)+.

Workup

  1. additionAfter the addition
  2. customquenched with 10% NaOH solution
  3. customThe solids were removed by filtration
  4. concentrationthe filtrate was concentrated in vacuum
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. dry with materialthe solution was dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-84fa2f6b76b74bac9bc50080b74a2d3d
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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