Sodium borohydride → HCID 86686043, compound

HRID 400441Notes

Reaction equation

HRID 400441 reaction equation
[BH4-].[Na+].[CH2:3]([N+:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]([CH3:21])=[CH:19][N:20]=2)=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([N:10]1[CH2:11][CH:12]=[C:13]([C:16]2[O:17][C:18]([CH3:21])=[CH:19][N:20]=2)[CH2:14][CH2:15]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86686044HCID 86686044, compound

Product 1

HCID 86686043HCID 86686043, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

21.6 g sodium borohydride was added to 130 g 1-benzyl-4-(5-methyl-oxazol-2-yl)-pyridinium in 1.5 L ethanol at 0° C. under nitrogen atmosphere. After 30 min at 0° C., the solution was stirred at RT for 2 h. The mixture was concentrated and treated with water and ethyl acetate. The organic layers were separated and aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated under vacuum. The resulting crude product was purified by flash chromatography (silica gel) to give 81.2 g of the desired product. Rf: 0.3 (petrolether/ethyl acetate:1/1), (M+H)+: 255

Workup

  1. concentrationThe mixture was concentrated
  2. additiontreated with water and ethyl acetate
  3. customThe organic layers were separated
  4. extractionaqueous layer was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe resulting crude product was purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-bcb274cf90ae4a709340b82b190fc8ef
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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