Sodium borohydride → HCID 18703633, compound

HRID 2287989Notes

Reaction equation

HRID 2287989 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[NH:6]1.[BH4-].[Na+]>CO>[OH:2][CH2:3][CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[NH:6]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12837909HCID 12837909, compound

Product 1

HCID 18703633HCID 18703633, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,3-Dihydro-3-oxo-1H-isoindole-1-acetic acid methyl ester (1.5 g, 7.5 mmol) is added to a solution of NaBH4 (1.4 g, 37.6 mmol) in 50 mL of methanol at room temperature, and the mixture is stirred overnight. The reaction is quenched by addition of gaseous HCl until the pH=1. The methanol is evaporated, and the remaining solid is stirred in 100 mL of CH2Cl2 for 15 minutes. The solid is removed by filtration through Celite® 545. Evaporation of the filtrate gives 1.3 g (90% yield) of 1,3-dihydro-3-(2-hydroxyethyl)-2H-isoindol-1-one as an oil.

Workup

  1. customThe reaction is quenched by addition of gaseous HCl until the pH=1
  2. customThe methanol is evaporated
  3. stirringthe remaining solid is stirred in 100 mL of CH2Cl2 for 15 minutes
  4. customThe solid is removed by filtration through Celite® 545
  5. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-a1a9a331f1b049579cd36cf81fb77add
Source dataset
uspto-grants-2000_07
Patent number
US06087364

Reaction notes

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