Sodium borohydride → HCID 58629904, compound

HRID 1391769Notes

Reaction equation

HRID 1391769 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:13])[CH2:9][CH2:10][O:11][CH3:12])[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.Cl>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:13])[CH2:9][CH2:10][O:11][CH3:12])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58629909HCID 58629909, compound

Product 1

HCID 58629904HCID 58629904, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 1-(6-bromo-2-pyridinyl)-3-(methyloxy)-1-propanone (547 mg, 2.24 mmol) in anhydrous MeOH (15 mL) under nitrogen at 0° C. was treated portion-wise with sodium borohydride (127 mg, 3.36 mmol) over 10 min. The resulting solution was stirred under nitrogen and gradually allowed to warm to room temperature over 2 h. The reaction mixture was then diluted with aqueous HCl (0.5M, 20 mL) and the resulting mixture extracted with EtOAc (2×50 mL). The combined organic layer was dried (MgSO4) and reduced under vacuum to afford the title compound as an off-white gum (551 mg).

Workup

  1. extractionthe resulting mixture extracted with EtOAc (2×50 mL)
  2. dry with materialThe combined organic layer was dried (MgSO4)

Sources & evidence

ORD record
ord-1e3eb0876d094cdfba0c2f2fde967cbb
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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