Tricyclo(3.3.1.13,7)dec-1-ylmethylamine → 1-(4-(Benzyloxy)phenyl)-2-((1-adamantylmethyl)amino)ethanol

HRID 75147

Reaktionsgleichung

Reaktionsgleichung von HRID 75147
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:17][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]12([CH2:28][NH2:29])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2>C(O)(C)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:16])[CH2:17][NH:29][CH2:28][C:18]23[CH2:27][CH:22]4[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]4)[CH2:25]2)[CH2:19]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 132487172-[4-(Benzyloxy)phenyl]oxirane

Produkt 1

HCID 594371761-(4-(Benzyloxy)phenyl)-2-((1-adamantylmethyl)amino)ethanolAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

2-(4-(benzyloxy)phenyl)oxirane (2 g, 8.8 mmol) and (1-adamantylmethyl)amine (1.46 g, 8.8 mol) were dissolved in isopropyl alcohol (30 mL) and heated under reflux overnight. The mixture was concentrated to give the crude product, which was purified by column chromatography to afford 1-(4-(benzyloxy)phenyl)-2-((1-adamantylmethyl)amino)ethanol (0.8 g, 23%). 1H NMR: (CDCl3, 400 MHz) δ=1.51 (m, 6H), 1.60-1.72 (m, 6H), 1.97 (m, 3H), 2.32&2.45 (dd, 2H), 2.64 (m, 1H), 2.73 (m, 1H), 2.94 (m, 1H), 3.40 (brs, 3H), 4.79 (m, 1H), 6.93 (m, 2H), 7.26-7.43 (m, 7H).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. concentrationThe mixture was concentrated
  4. customto give the crude product, which
  5. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-88047b6c7522438b9fa11d82686d0f95
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835426B2

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