Sodium borohydride → HCID 61256357, compound

HRID 912703Notes

Reaction equation

HRID 912703 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12](OC)=[O:13])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>CO>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][OH:13])[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67414926HCID 67414926, compound

Product 1

HCID 61256357HCID 61256357, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-butoxypyridine-2-carboxylate (1.20 g, 5.80 mmol, obtained from Example 18(b)) in methanol (60 mL) was added sodium borohydride (0.85 g, 23.0 mmol). The reaction was monitored by TLC (hexanes/ethyl acetate, 1:2). After the disappearance of starting material, the reaction mixture was concentrated in vacuo and the crude was dissolved in ethyl acetate/water (1:1, 60 mL). The aqueous layer was separated and extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and solvent was removed in vacuo to give the title compound (0.87 g, 84% yield) as a colorless oil.

Workup

  1. concentrationAfter the disappearance of starting material, the reaction mixture was concentrated in vacuo
  2. dissolutionthe crude was dissolved in ethyl acetate/water (1:1, 60 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-b3f740e18e77491ebbdfaecf27dc0fca
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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