Methanol → HCID 59635786, compound

HRID 470558Notes

Reaction equation

HRID 470558 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-bddca379a04348028c466720992b3fa2
Source dataset
uspto-grants-2014_01
Patent number
US08629138B2

Reaction notes

Loading…