Sodium borohydride → HCID 66637988, compound

HRID 1094994Notes

Reaction equation

HRID 1094994 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([CH:10]=[O:11])[S:7][C:6]=1[NH:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[O:4].[BH4-].[Na+]>O1CCCC1.CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([CH2:10][OH:11])[S:7][C:6]=1[NH:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86608144HCID 86608144, compound

Product 1

HCID 66637988HCID 66637988, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

Crude 2-(3,4-dimethoxy-benzoylamino)-5-formylthiophene-3-carboxylic acid methyl ester (35 mg) synthesized by the above process was dissolved in tetrahydrofuran/N,N-dimethylformamide=1/1 (10 ml). Sodium borohydride (22 mg) was added to the solution at room temperature, and the mixture was stirred at that temperature for 20 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to give crude 2-(3,4-dimethoxy-benzoylamino)-5-hydroxymethyl-thiophene-3-carboxylic acid methyl ester (35 mg, crude yield 100%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated under the reduced pressure

Sources & evidence

ORD record
ord-0a6a003670bc42c49f2766a4032242c2
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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