Sodium borohydride → HCID 68409208, compound

HRID 2194725Notes

Reaction equation

HRID 2194725 reaction equation
Cl.[CH3:2][NH:3][CH2:4][C:5]1[S:9][C:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=1.[BH4-].[Na+]>O1CCCC1.CO>[CH3:2][NH:3][CH2:4][C:5]1[S:9][C:8]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[OH:11])=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68411599HCID 68411599, compound

Product 1

HCID 68409208HCID 68409208, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The free base of {5-[(methylamino)methyl]-3-phenyl-2-thienyl}(phenyl)methanone (274 mg) obtained in Example 13 was dissolved in tetrahydrofuran (3 mL) and methanol (2 mL), and sodium borohydride (51 mg) was added at room temperature. After stirring for 3 hr, the solvent was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→1:9) to give a free base of the title compound (106 mg) as a pale-yellow oil. To a solution of fumaric acid (40 mg) in ethanol (3 mL) was added a solution of the obtained free base in ethyl acetate (4 mL), and the solvent was evaporated under reduced pressure. The residue was crystallized from a mixed solvent of ethyl acetate and 2-propanol and recrystallized from ethanol to give the title compound as colorless crystals (yield 40 mg, yield 32%).

Workup

  1. customthe solvent was evaporated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→1:9)

Sources & evidence

ORD record
ord-f8d7b4c0f9d34386bfd2aa14e561aa13
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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