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

HRID 6158Notes

Reaction equation

HRID 6158 reaction equation
[C:1]1(=[O:21])[N:5]([CH2:6][CH2:7][CH2:8][S:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:4](=[O:16])[C:3]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:2]12.[BH4-].[Na+].C(O)C.C(OCC)(=O)C>C(O)C>[OH:21][CH:1]1[C:2]2[C:3](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:4](=[O:16])[N:5]1[CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 190791181H-Isoindole-1,3(2H)-dione, 2-[3-(4-pyridinylthio)propyl]-HCID 21584252Ethanol ethylacetate

Product 1

HCID 571225054-[3-(3-Hydroxyisoindolin-1-on-2-yl)propylthio)pyridineYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.97 g (20.0 mmol) of 4-(3-phthalimidopropylthio)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 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: ethanol/ethyl acetate =1:10 to give 3.27 g of the desired compound (54.4% yield, colorless crystals), mp. 132°-134° C. NMR (200 MHz, CDCl3) δ: 2.11 (2H, m), 2.97 (2H, m), 3.72 (2H, m), 5.83 (1H, s), 6.98 (2H, d, J=5.4 Hz), 7.47-7.67 (3H, m), 7.77 (1H, dd, J=7.6, 1.2 Hz), 8.02 (2H, m).

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

Sources & evidence

ORD record
ord-f61c39e9b64e46f3aa67a30fba7b886d
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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