Triethylamine → 1-(4-Fluorophenyl)-5-(hydroxymethyl)-2(1H)-pyridinone

HRID 1630742Notes

Reaction equation

HRID 1630742 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15](O)=[O:16])=[CH:9]2)=[CH:4][CH:3]=1.CCN(CC)CC.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:9]=[C:10]([CH2:15][OH:16])[CH:11]=[CH:12][C:13]2=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydride2×HCID 584432461221423-61-5

Product 1

HCID 584433001-(4-Fluorophenyl)-5-(hydroxymethyl)-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

A 100 mL round-bottomed flask was charged with 1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid (1.8 g, 7.7 mmol) and 20 mL of THF. After cooling to −10° C., NEt3 (1.2 mL, 8.9 mmol) and ethyl chloroformate (0.84 mL, 8.5 mmol) were added. This mixture was stirred at that temp for 45 min, then an aq soln of NaBH4 (0.58 g, 15 mmol, in 10 mL of water) was added. After stirring for 3 h at −10° C., an additional 2 equiv of NaBH4 (solid) were added. The reaction was quenched with aq 1N HCl (50 mL) and extracted with CH2Cl2 (3×75 mL). The residue was purified by MPLC to give 1-(4-fluorophenyl)-5-(hydroxymethyl)pyridin-2(1H)-one.

Workup

  1. stirringAfter stirring for 3 h at −10° C.
  2. customThe reaction was quenched with aq 1N HCl (50 mL)
  3. extractionextracted with CH2Cl2 (3×75 mL)
  4. customThe residue was purified by MPLC

Sources & evidence

ORD record
ord-7630dce9b164405495a252fe7a3003ac
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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