Water → HCID 19831304, compound

HRID 1493356Notes

Reaction equation

HRID 1493356 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH:20]=[O:21])=[C:15]([CH3:19])[C:16]=1[O:17][CH3:18])=[O:11])[CH3:2].[BH4-].[Na+].O>C(O)C>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH2:20][OH:21])=[C:15]([CH3:19])[C:16]=1[O:17][CH3:18])=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19831295HCID 19831295, compound

Product 1

HCID 19831304HCID 19831304, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (±) N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-formyl-3-methoxy-4-methylthiophene-2-carboxamide (1.15 g) in ethanol (30 ml) was added sodium borohydride (0.154 g) in one portion. The solution was stirred at room temperature for 2 hours and then water (50 ml) added. After extraction with ethyl acetate, washing the organic extracts with water, drying over magnesium sulphate and filtering, the solvent was removed in vacuo to give the title compound as a golden oil, fumarate salt, m.p. 118°-119° C. (ex ethylacetate-ethanol ether as recrystallising solvent).

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washwashing the organic extracts with water
  3. dry with materialdrying over magnesium sulphate
  4. filtrationfiltering
  5. customthe solvent was removed in vacuo
  6. customto give
  7. customthe title compound as a golden oil, fumarate salt, m.p. 118°-119° C. (ex ethylacetate-ethanol ether as recrystallising solvent)

Sources & evidence

ORD record
ord-94628a74b5d2487ea6969d4a1ed26c36
Source dataset
uspto-grants-1991_06
Patent number
US05021449

Reaction notes

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