HCID 12523183, compound → 2-Pyridinepropanoic acid, methyl ester

HRID 1585454Notes

Reaction equation

HRID 1585454 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10]>CO.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 1

HCID 12523183HCID 12523183, compound

Product 1

HCID 100349532-Pyridinepropanoic acid, methyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 11b (2.0 g, 12.3 mmol) in 41 mL dry CH3OH was treated with 10% Pd-C (100.0 mg, 5 wt %) at room temperature under a hydrogen atmosphere (balloon) (10 h). The reaction mixture was then filtered through a Celite plug, washed with EtOAc (150 mL), and concentrated in vacuo. SGC chromatotron (SiO2, 4 mm, 15-50% EtOAc/hexanes) afforded 12b (1.97 g, 2.03 g theoretical, 97%). For 12b: -1H NMR (CDCl3, 250 MHz) d 8.39 (d, 1H, J=2.1 Hz, Pyr C6-H), 7.46 (m, 1H, Pyr C4-H), 6.90-7.15 (br m, 2H, J=7.7 Hz, Pyr C3-H and C5-H), 3.51, 3.52, and 3.54 (three s, total 3H, OCH3), 2.97 (m, 2H, PyrCH2), 2.69 (m, 2H, CH2 (C=O)); 13C NMR (CDCl3, 125 MHz) d 173.2, 159.7, 149.0, 136.1, 122.7, 121.1, 51.3, 32.8, 32.5; IR (neat) nmax 3009, 2951, 1738, 1593, 1569, 1475, 1437, 1367, 1199, 1168, 1097, 1052, 1027, 992, 841, 755 cm-1. See FIG. 18a.

Workup

  1. filtrationThe reaction mixture was then filtered through a Celite plug
  2. washwashed with EtOAc (150 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4695bac85c84e08a72bf2a5c809edd8
Source dataset
uspto-grants-1999_08
Patent number
US05939268

Reaction notes

Loading…