HCID 67329422, Verbindung → HCID 53373132, Verbindung

HRID 1846161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846161
C([O:8][C:9]1[C:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28]COC)=[N:11][C:12]([O:16][CH3:17])=[CH:13][C:14]=1[CH3:15])C1C=CC=CC=1>CO.Cl.[OH-].[OH-].[Pd+2]>[OH:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:10]1[C:9]([OH:8])=[C:14]([CH3:15])[CH:13]=[C:12]([O:16][CH3:17])[N:11]=1

Komponenten

5

Edukt 1

HCID 67329422HCID 67329422, Verbindung

Produkt 1

HCID 53373132HCID 53373132, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution containing 18 mg (0.04 mmol) of 3-(benzyloxy)-6-methoxy-2-(10-(methoxymethoxy)decyl)-4-methylpyridine in 3 mL of methanol were added two drops of concentrated HCl. The reaction mixture was stirred at reflux for 16 h. To the mixture were added 3 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/N). The reaction mixture was stirred at room temperature under hydrogen atmosphere for 15 min. The reaction mixture was filtered through celite and the filtrate was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (5×1 cm). Elution with 3:1 hexanes-ethyl acetate afforded the expected product as white solid: yield 8 mg (67%); mp: 80-81° C.; silica gel TLC Rf 0.50 (3:1 hexanes-ethyl acetate); 1H NMR (methanol-d4) δ 1.27 (br s, 12H), 1.49 (br s, 2H), 1.64 (br s, 2H), 2.41 (br s, 3H), 2.81 (br s, 2H), 3.51 (br s, 3H), 4.02 (br s, 1H) and 7.05 (br s, 1H); 13C NMR (methanol-d4) δ 16.59, 25.51, 28.13, 28.57, 28.92, 28.97, 29.09, 29.14, 29.24, 32.22, 56.39, 61.56, 107.60, 142.26, 145.27, 148.68 and 155.10; mass spectrum (APCI+), m/z 296.2220 (M+H) (C17H30NO3 requires 296.2226).

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. stirringThe reaction mixture was stirred at room temperature under hydrogen atmosphere for 15 min
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated under diminished pressure
  5. customThe residue was purified by chromatography on a silica gel column (5×1 cm)
  6. washElution with 3:1 hexanes-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1a24b973ea65410d8405d956195ab779
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952025B2

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