HCID 10559756, compound → HCID 12486248, compound

HRID 712475Notes

Reaction equation

HRID 712475 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C:8]1[C:9]([CH2:14][CH2:15][C:16](OCC)=[O:17])=[N:10][CH:11]=[CH:12][CH:13]=1>C1COCC1>[OH:17][CH2:16][CH2:15][CH2:14][C:9]1[C:8]([OH:7])=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 10559756HCID 10559756, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12486248HCID 12486248, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LiAlH4 (0.94 g) in THF was added ethyl 3-(3-hydroxypyridin-2-yl)propanoate (2.40 g) slowly at 0° C. The reaction mixture was stirred for 5 h at room temperature under N2, then cooled to rt and quenched with water at 0° C. The mixture was filtered. The filtrate was concentrated in vacuo to give the compound as yellow oil (0.95 g, 50%), and the crude product was used for the next step without further purification. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 154.7 (M+1).

Workup

  1. temperaturecooled to rt
  2. customquenched with water at 0° C
  3. filtrationThe mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ea86bdbe6729475a9dd8d6e5ebb38617
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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