HCID 11816706, compound → HCID 21218466, compound

HRID 1585455Notes

Reaction equation

HRID 1585455 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])=[CH:3][CH:2]=1>CO.[Pd]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 11816706HCID 11816706, compound

Product 1

HCID 21218466HCID 21218466, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 11c (3.14 g, 14.73 mmol) in 41 mL dry CH3OH was treated with 10% Pd-C (157.0 mg, 5 wt %) at room temperature under a hydrogen atmosphere (balloon) (8 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 12c (1.97 g, 2.03 g theoretical, 97%). For 12c: --H NMR (CDCl3, 250 MHz) d 8.77 (d, 1H, J=4.4 Hz, Ar C2-H), 8.08 (d, 1H, J=7.9 Hz, Ar C5-H or C8-H), 7.98 (d, 1H, J=7.6 Hz, Ar C5-H or Ar C8-H), 7.68 (ddd, 1H, J=1.5, 7.6, 7.9 Hz, Ar C6-H or C7-H), 7.54 (br dd, 1H, J=7.6, 7.9 Hz, Ar C6-H or C7-H), 7.21 (d, 1H, J=4.4 Hz, Ar C3-H), 3.65 (s, 3H, OCH3), 3.38 (t, 2H, J=7.7 Hz, ArCH2), 2.75 (t, 2H, J=7.7 Hz, CH2 (C=O)); IR (neat) nmax 2952, 1738, 1594, 1572, 1510, 1435, 1367, 124, 1170, 1026, 848, 763 cm-1. See FIG. 18b.

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-2720316acc184f73919f500da69c9332
Source dataset
uspto-grants-1999_08
Patent number
US05939268

Reaction notes

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