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

HRID 863994Notes

Reaction equation

HRID 863994 reaction equation
[C:1]1(=[O:22])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:4](=[O:17])[C:3]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:2]12.[BH4-].[Na+]>C(O)C>[OH:22][CH:1]1[C:2]2[C:3](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4](=[O:17])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14538888HCID 14538888, compound

Product 1

HCID 190790764-[4-(3-Hydroxyisoindolin-1-on-2-yl)butylthio]pyridineYield 27.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6.25 g (20.0 mmol) of 4-(4-phthalimidobutylthio)pyridine in 300 ml of ethanol, 1.51 g (40 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 2.5 hours. 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: ethyl acetate) to give 1.73 g of the desired compound (27.5% yield, colorless crystals), mp. 144°-145° 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: ethyl acetate)

Sources & evidence

ORD record
ord-2f8f50c86e2b4ea6a222e2dac0b3bf26
Source dataset
uspto-grants-1996_10
Patent number
US05561147

Reaction notes

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