Sodium borohydride → N-(4-fluoro-3-trifluoromethyl-benzyl)-N-[3-(1-hydroxy-ethyl)-benzo[b]thiophen-2-yl]-ethanesulfonamide

HRID 1511502Notes

Reaction equation

HRID 1511502 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[C:7]2[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=2[S:9][C:10]=1[N:11]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=1)[S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])(=[O:5])[CH3:4]>C(O)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:11]([C:10]2[S:9][C:8]3[CH:29]=[CH:30][CH:31]=[CH:32][C:7]=3[C:6]=2[CH:3]([OH:5])[CH3:4])[S:12]([CH2:15][CH3:16])(=[O:13])=[O:14])=[CH:19][C:20]=1[C:25]([F:28])([F:26])[F:27]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57920447N-(3-acetyl-benzo[b]thiophen-2-yl)-N-(4-fluoro-3-trifluoromethyl-benzyl)-ethanesulfonamide

Product 1

HCID 59147927N-(4-fluoro-3-trifluoromethyl-benzyl)-N-[3-(1-hydroxy-ethyl)-benzo[b]thiophen-2-yl]-ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.14 g, 3.7 mmol) was added to a solution of N-(3-acetyl-benzo[b]thiophen-2-yl)-N-(4-fluoro-3-trifluoromethyl-benzyl)-ethanesulfonamide (0.268 g, 0.582 mmol) in ethanol (10 mL), and the resulting mixture was stirred at room temperature for 3 h. The solvent was evaporated, the residue partitioned between dichloromethane and water, the organic layer separated, dried over sodium sulfate, filtered, and the solvent evaporated in vacuo to yield a residue. The residue was purified by flash column chromatography (SiO2), eluting with an ethyl acetate-heptane (10-40%) gradient to yield N-(4-fluoro-3-trifluoromethyl-benzyl)-N-[3-(1-hydroxy-ethyl)-benzo[b]thiophen-2-yl]-ethanesulfonamide as a colorless solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between dichloromethane and water
  3. customthe organic layer separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customto yield a residue
  8. customThe residue was purified by flash column chromatography (SiO2)
  9. washeluting with an ethyl acetate-heptane (10-40%) gradient

Sources & evidence

ORD record
ord-ef9950794bd34335aa1991043039248d
Source dataset
uspto-grants-2012_07
Patent number
US08216547B2

Reaction notes

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