Pyrrolidine → 1-[6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl]-pyrrolidine

HRID 418951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418951
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17]OS(C1C=CC(C)=CC=1)(=O)=O)[CH:12]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1)[CH:12]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Komponenten

4

Edukt 2

HCID 31268PyrrolidineHCID 72309434Toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester

Produkt 1

HCID 666521101-[6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl]-pyrrolidineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Combine toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester (0.087 g, 0.175 mmol), pyrrolidine (0.09 mL, 1.05 mmol), and benzene (5 mL), and reflux under nitrogen atmosphere. After 18 hours, concentrate reaction under vacuum then add ethyl acetate and wash with sodium bicarbonate solution (aq). Separate the organic phase and wash with brine. Dry the organic phase with anhydrous sodium sulfate and flash chromatograph using 2% to 4% (2M NH3 methanol)/methylene chloride to yield the titled compound (0.060 g, 86%) as a white solid. TLC Rf=0.25 in 4% 2M NH3 methanol:DCM. 1H NMR (CDCl3): 7.95 (d, 1H, J=8.4 Hz), 7.24 (d, 2H, J=8.4 Hz), 6.91 (m, 3H), 6.79 (dd, 1H, J=8.6, 2.4 Hz), 3.85 (s, 6H), 3.34 (t, 1H, J=9.2 Hz), 3.22 (s, 1H), 3.07 (dd, 1H, J=11.7, 3.3 Hz), 2.74 (dd, 1H, J=12.3, 7.5 Hz), 2.42 (m, 4H), 2.20 (m, 2H), 1.89 (m, 1H), 1.66 (m, 6H), 1.43 (m, 2H), 1.17 (m, 3H); MS m/z 406 (M+1).

Aufarbeitung

  1. concentrationconcentrate
  2. customreaction under vacuum
  3. washadd ethyl acetate and wash with sodium bicarbonate solution (aq)
  4. customSeparate the organic phase
  5. washwash with brine
  6. dry with materialDry the organic phase with anhydrous sodium sulfate and flash chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-d335e45a696345a8833f2d2979cc1898
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093302B2

Notizen zur Reaktion

Wird geladen…