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

HRID 964125Notes

Reaction equation

HRID 964125 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-435b5978552345e2872e92fb02bf00af
Source dataset
uspto-grants-1998_06
Patent number
US05767121

Reaction notes

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