Water → HCID 69879281, compound

HRID 379584Notes

Reaction equation

HRID 379584 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].O.C(=O)(O)[O-].[Na+].[CH:25]1([C:28](O)=O)[CH2:27][CH2:26]1>>[CH:25]1([CH2:28][NH:3][C:4]2[S:5][CH:6]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:27][CH2:26]1

Participants

6

Reactant 5

HCID 962WaterHCID 15655Cyclopropanecarboxylic acidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride3×HCID 52825623,4-Diethyl 2-aMinothiophene-3,4-dicarboxylate

Product 1

HCID 69879281HCID 69879281, compound

Procedure

Sodium borohydride (12.5 g) was added portionwise over 3 hours to a stirred solution of diethyl 2-aminothiophene-3,4-dicarboxyate (Example 36a, 25 g) in cyclopropane carboxylic acid (125 ml). The mixture was stirred at room temperature for 18 hours then further sodium borohydride (5 g) was added and stirring was continued at 50° C. for 16 hours. Further sodium borohydride (5 g) was again added and stirring was continued at 50° C. for 16 hours and then at room temperature for 3 days. Water (500 ml) was added, the mixture was neutralised with sodium bicarbonate and extracted with ether (2×250 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography over silica, eluting with ether/isohexane (2:3) to give the subtitle compound (12.10 g) as an oil.

Workup

  1. stirringstirring
  2. waitwas continued at 50° C. for 16 hours
  3. stirringstirring
  4. waitwas continued at 50° C. for 16 hours
  5. waitat room temperature for 3 days
  6. extractionextracted with ether (2×250 ml)
  7. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography over silica
  11. washeluting with ether/isohexane (2:3)

Sources & evidence

ORD record
ord-f046d097ccf04b63b699c3aeaa0003ea
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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