Sodium borohydride → HCID 54231897, compound

HRID 1607119Notes

Reaction equation

HRID 1607119 reaction equation
[CH2:1]([N:8]([C:13]1[CH:22]=[CH:21][C:16]([C:17](=[O:20])[CH2:18]Br)=[CH:15][CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH2:1]([N:8]([C:13]1[CH:22]=[CH:21][C:16]([CH:17]2[CH2:18][O:20]2)=[CH:15][CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13948318HCID 13948318, compound

Product 1

HCID 54231897HCID 54231897, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[N-Benzylmethanesulphonamido]phenacyl bromide (30 g) and sodium borohydride (4 g) in ethanol (500 ml) were stirred at room temperature for 18 hours. The solvent was then removed and the residue was taken up in ethyl acetate and washed three times with sodium bicarbonate solution and three times with brine. The organic phase was dried and evaporated to give an oil which was chromatographed on silica, "Kieselgel 60" (Merck, Trade Mark), eluting with methylene chloride. The product-containing fractions were combined and evaporated to give a solid which was triturated with hexane and filtered off to give the title compound, yield 13 g, m.p. 89°-92°.

Workup

  1. customThe solvent was then removed
  2. washwashed three times with sodium bicarbonate solution and three times with brine
  3. customThe organic phase was dried
  4. customevaporated
  5. customto give an oil which
  6. customwas chromatographed on silica, "Kieselgel 60" (Merck, Trade Mark)
  7. washeluting with methylene chloride
  8. customevaporated
  9. customto give a solid which
  10. customwas triturated with hexane
  11. filtrationfiltered off

Sources & evidence

ORD record
ord-dcadbeb1c8a44c1aa86eb0376d616f7e
Source dataset
uspto-grants-1989_09
Patent number
US04863948

Reaction notes

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