Sodium borohydride → HCID 68524228, compound

HRID 1932479Notes

Reaction equation

HRID 1932479 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=2)=[O:11])=[N:8][CH:9]=1)([O-:3])=[O:2].[BH4-].[Na+]>ClCCl.C(O)C>[OH:11][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1)[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68527540HCID 68527540, compound

Product 1

HCID 68524228HCID 68524228, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-[4-(5-nitropyridine-2-carbonyl)phenyl]propionate (1.52 g, 4.63 mmol) in dichloromethane (15 mL) and ethanol (15 mL) was added sodium borohydride (0.175 g, 4.63 mmol) under ice cooling, and the resulting solution was stirred at the same temperature for 1 hour. The reaction solution was concentrated under reduced pressure. The residue was dissolved in water and ethyl acetate. To the solution was added acetic acid and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), to thereby yield 0.264 g of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. additionTo the solution was added acetic acid
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-716c34fbf7484678be613a2c38073638
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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