Methanol → HCID 56610515, compound

HRID 1940184Notes

Reaction equation

HRID 1940184 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-benzyl-2-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 -350°, 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)-2,3-dihydro-1H-isoindole-1,3-dione as a colourless oil, IR (film): 3465 m (OH), 1772 s and 1708 s (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-54e9d691d60944ada8b6a523a1ae04d6
Source dataset
uspto-grants-1997_12
Patent number
US05698698

Reaction notes

Loading…