Sodium borohydride → HCID 12609442, compound

HRID 2287992Notes

Reaction equation

HRID 2287992 reaction equation
[BH4-].[Na+].C[O:4][C:5](=O)[CH2:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]1[CH3:17]>CO>[CH3:17][N:8]1[CH:7]([CH2:6][CH2:5][OH:4])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57321129Methyl 2,3-dihydro-2-methyl-3-oxo-1H-isoindole-1-acetate

Product 1

HCID 12609442HCID 12609442, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (4.1 g, 109.4 mmol) is added to a solution of 2,3-dihydro-2-methyl-3-oxo-1H-isoindole-1-acetic acid methyl ester (Synthesis, 1986:755) (4.8 g, 21.9 mmol) in 50 mL of MeOH at room temperature and stirred overnight. The reaction is quenched by addition of 100 mL of 2.0 N NaOH, and the MeOH is evaporated. The solution is extracted with CH2Cl2 (3×100 mL). The extracts are combined and dried over Na2SO4 and evaporated to give 2.2 g (52% yield) of 1,3-dihydro-2-methyl-3-(2-hydroxyethyl)-2H-isoindol-1-one.

Workup

  1. customThe reaction is quenched by addition of 100 mL of 2.0 N NaOH
  2. customthe MeOH is evaporated
  3. extractionThe solution is extracted with CH2Cl2 (3×100 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-78daec4284f94a84aed5463745c464e5
Source dataset
uspto-grants-2000_07
Patent number
US06087364

Reaction notes

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