Sodium borohydride → 3-[4-(3-Chlorophenyl)-1-ethyl-7-hydroxymethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid

HRID 1582992Notes

Reaction equation

HRID 1582992 reaction equation
C1COCC1.C(O)C.[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[N:21][C:22]([CH:26]=[O:27])=[CH:23][CH:24]=3)[N:19]([CH2:28][CH3:29])[C:18](=[O:30])[C:17]=2[CH2:31][CH2:32][C:33]([O:35]C)=[O:34])[CH:13]=[CH:14][CH:15]=1.[BH4-].[Na+]>O>[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[N:21][C:22]([CH2:26][OH:27])=[CH:23][CH:24]=3)[N:19]([CH2:28][CH3:29])[C:18](=[O:30])[C:17]=2[CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21873804Tetrahydrofuran ethanolHCID 22716671Methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate

Product 1

HCID 227167153-[4-(3-Chlorophenyl)-1-ethyl-7-hydroxymethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acidYield 44.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 7 ml THF-ethanol (5:2) solution containing 300 mg of methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate was added 9 mg of sodium borohydride under ice cooling. After stirring for 1 hour, water was added to the reaction mixture and the whole was extracted with ethyl acetate. The organic layer was washed with saturated brine and then the solvent was evaporated. The residue was purified by a silica gel column chromatography (hexane-ethyl acetate). Using a 200 mg portion of 210 mg of the resulting compound, the compound was treated in a similar manner to Example 2 to obtain 130 mg of 3-[4-(3-chlorophenyl)-1-ethyl-7-hydroxymethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid as pale yellow crystals.

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. customThe residue was purified by a silica gel column chromatography (hexane-ethyl acetate)
  5. additionthe compound was treated in a similar manner to Example 2

Sources & evidence

ORD record
ord-bcd2d925c3fd4e679edc41f5bd15465e
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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