Sodium borohydride → N-[(1R)-1-[4-(1-Hydroxyethyl)phenyl]ethyl]methanesulfonamide

HRID 880241Notes

Reaction equation

HRID 880241 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH3:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CCO>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C@H:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH3:11])=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117774699N-[(1R)-1-(4-Acetylphenyl)ethyl]methanesulfonamide

Product 1

HCID 117774719N-[(1R)-1-[4-(1-Hydroxyethyl)phenyl]ethyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve N-[(1R)-1-(4-acetylphenyl)ethyl]methanesulfonamide (15 g, 62 mmol) in EtOH (155.4 mL) and cool with an ice bath. Add sodium borohydride (1.2 g, 31.1 mmol) and stir the resulting mixture in the ice bath for 2 h. Quench the reaction with H2O (20 mL) and concentrate under reduced pressure. Dilute the residue with EtOAc (90 mL) and H2O (50 mL). Separate the layers and wash the organic layer with brine (2×50 mL), dry over MgSO4; filter; and concentrate the filtrate under reduced pressure to provide a residue. Purify and separate isomers using chromatography conditions K (see below) collecting the second eluting isomer as the title compound (2.01 g, 13%). MS (m/z): 261 (M+18).

Workup

  1. temperaturecool with an ice bath
  2. customQuench
  3. customthe reaction with H2O (20 mL)
  4. concentrationconcentrate under reduced pressure
  5. additionDilute the residue with EtOAc (90 mL) and H2O (50 mL)
  6. customSeparate the layers
  7. washwash the organic layer with brine (2×50 mL)
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. concentrationand concentrate the filtrate under reduced pressure
  11. customto provide a residue
  12. customPurify
  13. customseparate isomers
  14. customcollecting the second eluting isomer as the title compound (2.01 g, 13%)

Sources & evidence

ORD record
ord-b19d78a518cd4133b7a8190d35af8f65
Source dataset
uspto-grants-2015_03
Patent number
US08993568B2

Reaction notes

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