Sodium borohydride → 3-Bromo4-(N,N-dimethylsulfamoyl)benzyl alcohol

HRID 19950Notes

Reaction equation

HRID 19950 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])[CH:5]=[O:6].[BH4-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 219769193-Bromo-4-(N,N-dimethylsulfamoyl)benzaldehyde

Product 1

HCID 657510183-Bromo4-(N,N-dimethylsulfamoyl)benzyl alcoholYield 96.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of OBS02001 (6.0 g, 19.47 mmol) in anhydrous THF (50 mL) was added sodium borohydride (0.81 g, 21.42 mmol). The mixture was stirred at room temperature for 4 h, quenched with water (CARE!!) and filtered through a Celite pad. The filtrate was concentrated in vacuo and re-dissolved in DCM (200 mL). The organic layer was washed with brine (2×200 mL), dried (Na2SO4) and filtered. Concentration in vacuo of the filtrates gave OBS02002 as a pale yellow oil (5.54 g, 92%). TLC [SiO2, EtOAc-n-hexane (1:1)] RF=0.47; 1H-NMR (270 MHz, CDCl3)=2.97 (6H, s), 3.14 (1H, bs, OH), 4.51 (2H, s) 7.19 (1H, dd, J=1.5, 8.1), 7.37 (1H, d, J=8.4), 7.52 (1H, d, J=1.8).

Workup

  1. customquenched with water (CARE!!)
  2. filtrationfiltered through a Celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionre-dissolved in DCM (200 mL)
  5. washThe organic layer was washed with brine (2×200 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationConcentration in vacuo of the filtrates

Sources & evidence

ORD record
ord-53ab4231f29240a29163922b636fb36f
Source dataset
uspto-grants-2010_06
Patent number
US07745472B2

Reaction notes

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