Sodium borohydride → HCID 69037022, compound

HRID 1820780Notes

Reaction equation

HRID 1820780 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:30](=[O:32])[CH3:31])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[C:15]2[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:16]=2[O:25][CH:26]([CH3:28])[CH3:27])[CH2:10][CH2:9]1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:30]([OH:32])[CH3:31])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:15]2[CH:20]=[C:19]([S:21]([CH3:24])(=[O:22])=[O:23])[CH:18]=[CH:17][C:16]=2[O:25][CH:26]([CH3:28])[CH3:27])=[O:29])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11488045HCID 11488045, compound

Product 1

HCID 69037022HCID 69037022, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.086 mmol of 1-{3-Fluoro-4-[4-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-phenyl}-ethanone was dissolved in 1 ml ethanol and 0.26 mmol sodium borohydride was added. The mixture was refluxed for 40 min., cooled to room temperature, quenched with water, acidified with HCl 1N and extracted with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was purified on silica eluting with heptane/ethylacetate to yield after evaporation the title compound. MS (m/e): 465.4 (M+H+, 100%)

Workup

  1. temperatureThe mixture was refluxed for 40 min.
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified on silica eluting with heptane/ethylacetate
  8. customto yield
  9. customafter evaporation the title compound

Sources & evidence

ORD record
ord-cce7ee209bde4d83befef1cb2c9d87fd
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

Loading…