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

HRID 6152Notes

Reaction equation

HRID 6152 reaction equation
[C:1]1(=[O:20])[N:5]([CH2:6][CH2:7][S:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[C:3]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:2]12.[BH4-].[Na+]>C(O)C>[OH:20][CH:1]1[C:2]2[C:3](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:4](=[O:15])[N:5]1[CH2:6][CH2:7][S:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 190792564-(2-Phthalimidoethylthio)pyridine

Product 1

HCID 190792374-[2-(3-Hydroxyisoindolin-1-on-2-yl)ethylthio]pyridineYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.69 g (20.0 mmol) of 4-(2-phthalimidoethylthio)pyridine in 150 ml of ethanol, 2.27 g (60 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 15 minutes. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chloroform and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10), after which subsequent recrystallization from ethyl acetate gave 3.63 g of the desired compound (63.4% yield, colorless crystals), mp. 111.5°-112.5° C.

Workup

  1. distillationThe solvent was distilled off
  2. additionsaturated saline was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialthe extract was dried 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. customafter which subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-971581ad4e8b4fdcb8263bf8c74245a7
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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