Sodium Hydroxide → HCID 22335509, compound

HRID 349393Notes

Reaction equation

HRID 349393 reaction equation
[BH4-].[Na+].Cl[CH:4]([CH3:27])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:26])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)=[CH:9][CH:8]=1)=[O:6].[OH-].[Na+]>CO>[CH3:25][O:24][C:18]1[CH:17]=[C:16]([CH2:15][C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([CH:5]3[CH:4]([CH3:27])[O:6]3)=[CH:8][CH:9]=2)=[O:26])[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 18353437HCID 18353437, compound

Product 1

HCID 22335509HCID 22335509, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium tetrahydroborate (0.0502 mol) was added portionwise at 0° C. to a mixture of (±)-N-[4-(2-chloro-1-oxopropyl)phenyl]-3,4-dimethoxybenzeneacetamide (0.0502 mol) in methanol (280 ml). The mixture was stirred at 0° C. for 1 hour, then poured out into a mixture of NaOH (280 ml) and ice, stirred for 1 hour and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 15.48 g (94%) of (±)-3,4-dimethoxy-N-[4-(3-methyl-2-oxiranyl)phenyl]benzeneacetamide (interm. 11).

Workup

  1. stirringstirred for 1 hour
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cb127a1129c04ac1835b141e6c9ca90d
Source dataset
uspto-grants-2007_02
Patent number
US07179825B2

Reaction notes

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