Sodium borohydride → HCID 68562257, compound

HRID 901188Notes

Reaction equation

HRID 901188 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:16])[C:9]=1[S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])[CH:5]=[O:6].[BH4-].[Na+]>C1COCC1>[Br:16][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([Br:1])[C:9]=1[S:10](=[O:15])(=[O:14])[N:11]([CH3:12])[CH3:13])[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 219768843,5-Dibromo4-(n,n-dimethylsulfamoyl)benzaldehyde

Product 1

HCID 68562257HCID 68562257, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of OBS02013 (5.5 g, 14.21 mmol) in anhydrous THF (50 mL) was added sodium borohydride (0.59 g, 15.63 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 combined filtrates gave OBS02015 as a pale yellow oil (5.21 g, 94%). TLC [SiO2, EtOAc-n-hexane (1:1)] Rf=0.55; 1H-NMR (270 MHz, CDCl3)=1.97 (1H, bs, OH), 3.11 (6H, s), 4.63 (2H, s), 7.55 (2H, t, J=1.5).

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 combined filtrates

Sources & evidence

ORD record
ord-98f30a14bec04fea9239dcfc0e1501ca
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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