Methanol → HCID 68254813, Verbindung

HRID 1668499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1668499
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][C:13]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([N+:25]([O-])=O)=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[CH:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].O.NN.[CH3:31]O>[Ni]>[NH2:25][C:21]1[CH:20]=[C:19]2[C:24]([C:16]([C:13]3[CH2:14][CH2:15][CH:10]([N:2]([CH2:1][CH3:31])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH2:11][CH:12]=3)=[CH:17][NH:18]2)=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 59004649tert-Butyl methyl(4-(6-nitro-1H-indol-3-yl)cyclohex-3-enyl)carbamate

Produkt 1

HCID 68254813HCID 68254813, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 935NickelKatalysator

Versuchsvorschrift

A solution of compound 127 (0.2 g, 0.518 mmol) in dry MeOH (3 mL) was treated with Ra—Ni (0.02 g) followed by hydrazine hydrate (0.16 mL, 5.188 mmol) at room temperature. The reaction was placed in a pre-heated oil bath and refluxed for 2 min. The reaction brought to room temperature, filtered through celite bed and washed with methanol (2×15 mL). The solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 2.5:97.5) to obtain compound 130 as a foam. 1H NMR (DMSO-d6) δ 1.08 (t, 3H, J=6.9 Hz), 1.41 (s, 9H), 1.72-1.89 (m, 2H), 2.18-2.60 (m, 4H), 3.10-3.20 (m, 2H), 4.01 (brs, 1H), 4.71 (s, 2H), 6.02 (brs, 1H), 6.39 (dd, 1H, J=1.5, 8.5 Hz), 6.51 (d, 1H, J=1.8 Hz), 6.99 (d, 1H, J=2.1 Hz), 7.43 (d, 1H, J=8.4 Hz), 10.44 (s, 1H); ESI-MS (m/z, %): 378 (M+Na, 8), 356 (MH+,4), 300 (100).

Aufarbeitung

  1. customThe reaction was placed in a pre-heated oil bath
  2. temperaturerefluxed for 2 min
  3. custombrought to room temperature
  4. filtrationfiltered through celite bed
  5. washwashed with methanol (2×15 mL)
  6. customThe solvent was evaporated
  7. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 2.5:97.5)

Quellen und Nachweise

ORD-Eintrag
ord-1e998cc7cec741d288b04378a7306c6d
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989447B2

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