Hydroxyamine hydrochloride → tert-butyl 5-(1-aminoethyl)-4-chloro-1H-indole-1-carboxylate

HRID 475308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475308
C(=[N:14][CH:15]([C:17]1[C:18]([Cl:33])=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=[CH:20]2)[CH3:16])(C1C=CC=CC=1)C1C=CC=CC=1.Cl.NO>CO>[NH2:14][CH:15]([C:17]1[C:18]([Cl:33])=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=[CH:20]2)[CH3:16]

Komponenten

4

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 86694759tert-butyl 5-[1-(benzhydrylideneamino)ethyl]-4-chloro-1H-indole-1-carboxylate

Produkt 1

HCID 86694760tert-butyl 5-(1-aminoethyl)-4-chloro-1H-indole-1-carboxylateAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a stirred solution of 324 (880.0 mg, 1.92 mmol) in anhydrous MeOH (20 mL) was added hydroxylamine hydrochloride (532.9 mg, 7.70 mmol), and the reaction mixture was stirred at 40° C. under N2 for 16 h. Volatile solvents were removed in vacuo, and the residue was diluted with EtOAc. The organic layer was washed with sat'd. aq. NaHCO3, water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/heptane gradient (20 to 100% EtOAc), followed a MeOH/EtOAc (+1% TEA) gradient (0 to 80% MeOH) to afford 290 mg (51.3%) of tert-butyl 5-(1-aminoethyl)-4-chloro-1H-indole-1-carboxylate (326) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.99 (d, J=8.7 Hz, 1H), 7.73 (d, J=3.7 Hz, 1H), 7.64 (d, J=8.7 Hz, 1H), 6.71 (d, J=3.7 Hz, 1H), 4.49 (d, J=6.6 Hz, 1H), 2.36-1.90 (m, 2H), 1.63 (s, 9H), 1.26 (d, J=6.6 Hz, 3H).

Aufarbeitung

  1. customVolatile solvents were removed in vacuo
  2. additionthe residue was diluted with EtOAc
  3. washThe organic layer was washed with sat'd
  4. dry with materialaq. NaHCO3, water and brine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with an EtOAc/heptane gradient (20 to 100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-10e38649ab7d4f74a43cade0285c3a1f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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