Methanol → HCID 56610515, compound

HRID 1684693Notes

Reaction equation

HRID 1684693 reaction equation
[CH2:1]([CH:8]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])[CH:9]([OH:14])[CH2:10][N+]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][O-:27].[Na+].S(=O)(=O)(O)O.C(Cl)Cl.[CH3:37][OH:38]>>[CH2:1]([C@H:8]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])[C@H:9]([OH:14])[CH:10]([O:38][CH3:37])[O:27][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 887Methanol3×HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 10942334Sodium MethoxideHCID 21466130HCID 21466130, compound

Product 1

HCID 56610515HCID 56610515, compoundYield 49%

Procedure

A suspension of 1.02 g of an 87:13 mixture of the (1S,2R) and (1S,2S) isomers of 2-(1-benzyl2-hydroxy-3-nitropropyl)-2,3-dihydro-1H-isoindole-1,3-dione in 2 ml of methanol is treated at 0° with 5.7 ml of a 7% solution of sodium methylate in methanol and the resulting yellow solution is added dropwise over a period of 20 minutes to a solution, cooled to -35°, of 7.2 ml of sulfuric acid in 27.6 ml of methanol. The reaction mixture is subsequently added to a stirred mixture of 150 ml of methylene chloride and 70 ml of ice-water and the aqueous phase is extracted with methylene chloride. The combined methylene chloride phases were dried, filtered and concentrated, and the residue was purified on silica gel with hexane/ethyl acetate (3:1). After evaporation and drying there is obtained 0.52 g (49%) of pure (1S,2S)-2-(1-benzyl-2-hydroxy-3,3-dimethoxypropyl)-2,3dihydro-1H-isoindole-1,3dione as a colourless oil, IR (film): 3465m (OH), 1772s and 1708s (C=O of imide), 1071 s (C--O--C).

Workup

  1. additionthe resulting yellow solution is added dropwise over a period of 20 minutes to a solution
  2. extractionthe aqueous phase is extracted with methylene chloride
  3. dry with materialThe combined methylene chloride phases were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified on silica gel with hexane/ethyl acetate (3:1)
  7. customAfter evaporation
  8. customdrying there

Sources & evidence

ORD record
ord-b8513f1babe24b2e9625c406d02256f0
Source dataset
uspto-grants-1997_06
Patent number
US05641886

Reaction notes

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