Sodium borohydride → HCID 54140687, compound

HRID 1708111Notes

Reaction equation

HRID 1708111 reaction equation
[BH4-].[Na+].[CH3:3][O:4][N:5]=[C:6]([C:9]1[CH2:10][N+:11](=[O:15])[CH:12]=[CH:13][CH:14]=1)[C:7]#[N:8]>CO.O>[CH3:3][O:4][N:5]=[C:6]([C:9]1[CH2:10][N:11]([OH:15])[CH2:12][CH2:13][CH:14]=1)[C:7]#[N:8]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86748192HCID 86748192, compound

Product 1

HCID 54140687HCID 54140687, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

Sodium borohydride (0.13 g, 0.0034 mol) was added to a mixture of methanol (5 ml) and water (5 ml) at 0° C. To this was added dropwise a solution of α-(methoxyimino)-α-(1-oxopyridinium-3-yl)acetonitrile (D5) (0.2 g, 0.0011 mol) in methanol (30 ml) and water (5 ml). The mixture was allowed to warm to room temperature and stirred for a further 2 h. The mixture was evaporated to dryness and the residue partitioned between saturated aqueous potassium carbonate (25 ml) and chloroform(3×30 ml). The organic extracts were combined and dried (Na2SO4) then filtered and evaporated to dryness. The residue was subjected to column chromatography on silica gel eluting with 0-2% methanol/chloroform to give a solid which was recrystallised from ethyl acetate/pentane to afford the title compound (E2) as a white crystalline solid (0.135 g, 67%) m.p. 145°-147° C.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue partitioned between saturated aqueous potassium carbonate (25 ml) and chloroform(3×30 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationthen filtered
  5. customevaporated to dryness
  6. customto give a solid which
  7. customwas recrystallised from ethyl acetate/pentane

Sources & evidence

ORD record
ord-8bc9cfacf05544988c240a5f2e23af01
Source dataset
uspto-grants-1994_10
Patent number
US05356914

Reaction notes

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