Sodium borohydride → 4-[3-(3-Hydroxyisoindolin-1-on-2-yl)propyloxy]pyridine

HRID 6149Notes

Reaction equation

HRID 6149 reaction equation
[BH4-].[Na+].[C:3]1(=[O:23])[N:7]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:6](=[O:18])[C:5]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:4]12>C(O)C>[OH:23][CH:3]1[C:4]2[C:5](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:6](=[O:18])[N:7]1[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 190790904-(3-Phthalimidopropyloxy)pyridine

Product 1

HCID 190791984-[3-(3-Hydroxyisoindolin-1-on-2-yl)propyloxy]pyridineYield 54.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride [1.89 g (50 mmol)] was added to a solution of 2.82 g (10.0 mmol) of 4-(3-phthalimidopropyloxy)pyridine in 150 ml of ethanol. The mixture was stirred at room temperature for 15 minutes. After the solvent was distilled off, brine was added to the residue. The mixture was extracted with chloroform and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10), and then recrystallized from ethyl acetate to obtain 1.54 g of the desired compound (yield: 54.2%, colroless crystals).

Workup

  1. distillationAfter the solvent was distilled off
  2. additionbrine was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-65c49a041cb1404cbaeaf61fdae85da3
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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