Sodium Bicarbonate → 3,3''-Dimethyl-1',2',3',4',5', 6'-hexahydro-cis-[2,2';6',2'']terpyridine

HRID 1987316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987316
C([N:4]1[C@H:9]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:8][CH2:7][CH2:6][C@@H:5]1[C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=1)C=C.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][C:15]1[C:10]([C@H:9]2[CH2:8][CH2:7][CH2:6][C@@H:5]([C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=3)[NH:4]2)=[N:11][CH:12]=[CH:13][CH:14]=1

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 674222901'-Allyl-3,3''-dimethyl-1',2',3',4',5',6'-hexahydro-cis-[2,2'; 6',2'']terpyridine

Produkt 1

HCID 575911373,3''-Dimethyl-1',2',3',4',5', 6'-hexahydro-cis-[2,2';6',2'']terpyridineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1′-allyl-3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-cis-[2,2′;6′,2″]terpyridine (142 mg, 0.462 mmol) in CH2Cl2 was added 1,3-dimethylbarbaturic acid (361 mg, 2.31 mmol) and Pd(PPh3)4 (53 mg, 0.046 mmol) and the reaction mixture was stirred for 20 h. Saturated solution of NaHCO3 (10 mL) was added and the mixture was extracted with CH2Cl2 (3 times 20 mL). The organic extracts were dried (MgSO4), filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (9:1:0.2 CH2Cl2-MeOH—NH4OH) to provide 105 mg (85%) of the 3,3″-dimethyl-1′,2′,3′,4′,5′, 6′-hexahydro-cis-[2,2′;6′,2″]terpyridine as a clear oil. 1H NMR(CDCl3) δ 1.51-1.63 (m, 2H), 1.76-1.85 (m, 3H), 2.11-2.15 (m, 1H), 2.37 (s, 6H), 3.10-3.30 (m, 1H), 4.22 (d, 2H, J=10.8 Hz), 7.02 (dd, 2H, J=7.5, 4.5 Hz), 7.38 (d, 2H, J=7.5 Hz), 8.45 (d, 2H, J=4.5 Hz); 13C NMR (CDCl3) δ 18.68, 25.84, 32.28, 57.60, 121.96, 129.73, 138.04, 147.31, 160.94; ES-MS m/z 269.1 (M+H). Anal. Calcd. for C17H21N3.0.1CH2Cl2: C, 74.45; H, 7.75; N, 15.23. Found: C, 74.70; H, 7.80; N, 15.18.

Aufarbeitung

  1. extractionthe mixture was extracted with CH2Cl2 (3 times 20 mL)
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash column chromatography on silica gel (9:1:0.2 CH2Cl2-MeOH—NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-bb81ad8e1fbd414a8c17891a7401612a
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550484B2

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