Sodium borohydride → HCID 23084549, compound

HRID 2111633Notes

Reaction equation

HRID 2111633 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH:5]2[CH2:19][C:20](OCC)=[O:21].[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH:5]2[CH2:19][CH2:20][OH:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23084543HCID 23084543, compound

Product 1

HCID 23084549HCID 23084549, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5,6-dimethyl-3-ethoxycarbonylmethyl-2-(3-pyridyl)isoindolin-1-one [IUPAC name: ethyl 2-[5,6-dimethyl-3-oxo-2-(3-pyridinyl)-2,3-dihydro-1H-isoindol-1-yl]acetate] (8.4 g, 26 mmol) in methanol (250 ml) was added by portions sodium borohydride (11 g, 0.52 mmol), and the reaction mixture was stirred with heating at 80° C. for 3 hrs. To the reaction solution was added ice-cold water, and the precipitated crystals were collected by filtration, washed with water, and dried to give 6.0 g of 5,6-dimethyl-2-(3-pyridyl)-3-(2-hydroxyethyl)isoindolin-1-one.

Workup

  1. additionTo the reaction solution was added ice-cold water
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ea37eab8e51842fcb3c4bce78aeb56d6
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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