Hydrochloric Acid → HCID 68882717, Verbindung

HRID 1269492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269492
[CH2:1]([O:3][C:4](=[O:21])[C:5]([CH3:20])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:9]=1)[CH3:6])C.Cl.[H][H]>CO.[Pt]>[CH3:1][O:3][C:4](=[O:21])[C:5]([CH3:6])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]2[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)[CH:9]=1)[CH3:20]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 688835012-Methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 68882717HCID 68882717, VerbindungAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

2-methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl ester (6.0 g, 21.03 mmol) was dissolved in methanol (70 mL) and followed by the addition of 37% HCl (5.3 mL) and 10% Pt/C (0.60 g). The mixture was shaken with hydrogen under 50 psi at 50° C. in a Parr bottle for 5 h, filtered through a pad of Celite, and rinsed with methanol. GC/MS showed complete hydrogenation and only 50% of methyl ester conversion. Concentrated H2SO4 (2.0 mL) was added to the filtrate and the resulting solution was allowed to reflux under nitrogen overnight. After removal of excess methanol, the residue was treated with saturated Na2CO3 (150 mL) and extracted with ethyl acetate (2×200 mL). The organic extract was washed with water, dried over sodium sulfate, and concentrated to give 4.80 g (82%) of 2-methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid methyl ester as a yellow oil: 1H NMR (CDCl3) δ 1.59 (s, 6H), 1.78 (br, 1H), 1.97 (br d, 1H), 2.02 (br, 2H), 2.61 (m, 3H), 3.06 –3.13 (m, 2H), 3.76 (s, 3H), 6.61 (dd, 1H), 6.70 (s, 1H), 6.83 (d, 1H), 7.14 (t, 1H); MS m/z (relative intensity) 277 (M+, 2), 218 (6), 176 (100).

Aufarbeitung

  1. filtrationfiltered through a pad of Celite
  2. washrinsed with methanol
  3. additionConcentrated H2SO4 (2.0 mL) was added to the filtrate
  4. temperatureto reflux under nitrogen overnight
  5. customAfter removal of excess methanol
  6. additionthe residue was treated with saturated Na2CO3 (150 mL)
  7. extractionextracted with ethyl acetate (2×200 mL)
  8. extractionThe organic extract
  9. washwas washed with water
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dae6c3e96cb84550895e2a450a6463c5
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199243B2

Notizen zur Reaktion

Wird geladen…