Sodium borohydride → HCID 19833124, compound

HRID 1639387Notes

Reaction equation

HRID 1639387 reaction equation
[BH4-].[Na+].[C:3]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([C:12]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:13]=1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:11])(=[O:5])[CH3:4]>CO>[C:3]([NH:6][CH2:7][CH2:8][CH2:9][CH:10]([C:12]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:13]=1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[OH:11])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19833136HCID 19833136, compound

Product 1

HCID 19833124HCID 19833124, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.38 g (0.01 mol) of sodium borohydride is added to a solution of 3.25 g (0.01 mol) of methyl 2-(4-acetamidobutyryl)-5-chloro-hydrocinnamate in 35 ml of methanol and the mixture is stirred at room temperature for 1 hour. The solution is concentrated, extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography on silica gel with chloroform-methanol (20:1) gives methyl 2-(4-acetamido-1-hydroxybutyl)-5-chlorohydrocinnamate as a yellow oil.

Workup

  1. concentrationThe solution is concentrated
  2. extractionextracted with methylene chloride/water
  3. dry with materialdried with magnesium sulfate
  4. distillationthe solvent is distilled in a vacuum

Sources & evidence

ORD record
ord-57d5655bf6a74accae585dfd3f68002b
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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