3-Benzyloxy-2-methyl-1-(2-pivaloyloxyethyl)pyridin-4-one → 3-Hydroxy-2-methyl-1-(2-pivaloyloxyethyl)pyridin-4-one

HRID 374445Notes

Reaction equation

HRID 374445 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]=1[CH3:25])C1C=CC=CC=1>[Pd].CN(C)C=O>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:22])([CH3:21])[CH3:23])[C:10]=1[CH3:25]

Participants

4

Reactant 1

HCID 189971743-Benzyloxy-2-methyl-1-(2-pivaloyloxyethyl)pyridin-4-one

Product 1

HCID 98379203-Hydroxy-2-methyl-1-(2-pivaloyloxyethyl)pyridin-4-oneYield 77.46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

3-Benzyloxy-2-methyl-1-(2-pivaloyloxyethyl)pyridin-4-one (1.08 g, 0.003 mol) was hydrogenated over Pd/C catalyst in dimethylformamide (30 ml) with stirring for 24 hours. The solution was filtered and rotary evaporated to dryness to provide a crude product (1.08 g) which was flash chromatographed (silica gel, Kieselgel 60,7734, 20 mm×300 mm column, eluting with ethyl acetate:ethanol, 1:1 v/v). Rotary evaporation in vacuo at 60° C. provided the title compound in 77.46% yield as orange crystals, m.p. 147°-149° C.; νmax 1580, 1625, 1725, 2850 cm-1 ; δ(d6 dimethylsulphoxide) 1.1 (9H,s), 2.35 (3H,s), 4.30 (4H,s), 4.4 (1H,s), 6.15 (1H,d), 7.55 (1H,d).

Workup

  1. filtrationThe solution was filtered
  2. customrotary evaporated to dryness
  3. customto provide a crude product (1.08 g) which
  4. customchromatographed
  5. wash(silica gel, Kieselgel 60,7734, 20 mm×300 mm column, eluting with ethyl acetate:ethanol, 1:1 v/v)
  6. customRotary evaporation in vacuo at 60° C.

Sources & evidence

ORD record
ord-0adfc3c97aff43608be51762dafd900e
Source dataset
uspto-grants-1996_01
Patent number
US05480894

Reaction notes

Loading…