Methanol → HCID 59635786, compound

HRID 406769Notes

Reaction equation

HRID 406769 reaction equation
[BH4-].[Li+].C[O:4][C:5](=O)[C:6]([CH3:17])([CH3:16])[CH2:7][N:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]1=[O:15].CO>O1CCCC1.[O-]S([O-])(=O)=O.[Mg+2]>[Br:14][C:11]1[CH:12]=[CH:13][N:8]([CH2:7][C:6]([CH3:16])([CH3:17])[CH2:5][OH:4])[C:9](=[O:15])[CH:10]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 59635660HCID 59635660, compound

Product 1

HCID 59635786HCID 59635786, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 24083Sulfuric acid magnesium salt (1:1)Solvent

Procedure

Lithium borohydride (25 mg) was added to a solution of 3-(4-bromo-2-oxo-2H-pyridin-1-yl)-2,2-dimethyl-propionic acid methyl ester (0.29 g) in tetrahydrofuran (3 mL) chilled in an ice bath. Then methanol (45 μL) was added and the mixture was stirred in the cooling bath for 1 h and at room temperature overnight. The mixture was diluted with tetrahydrofuran and MgSO4 was added. The mixture was filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:1) to afford the title compound as a colorless oil. Yield: 0.13 g (49% of theory); Mass spectrum (ESI+): m/z=260/262 (Br) [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. additionwas added
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-3ab8c4e009b64e15a7a567fa6219fa0d
Source dataset
uspto-grants-2014_06
Patent number
US08754076B2

Reaction notes

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