Methanol → Tricyclo(3.3.1.13,7)dec-1-ylmethylamine

HRID 75141

Reaktionsgleichung

Reaktionsgleichung von HRID 75141
[C:1]12([C:11]([NH2:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(C)C.CO>C1COCC1>[C:1]12([CH2:11][NH2:13])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Komponenten

5

Edukt 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 21686Tricyclo(3.3.1.13,7)decane-1-carboxamide

Produkt 1

HCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of admantane-1-carboxamide (2 g, 11.17 mmol) in THF (50 mL) was added BH3.Me2S (10.2 M, 3.4 mL, 34.7 mmol) under nitrogen. The mixture was heated at reflux overnight. The solution was cooled to rt. Methanol (20 mL) was added to the solution. The mixture was concentrated under vacuum to give crude product, which was purified by chromatography on silica gel to afford (1-adamantyl)methylamine (1.09 g, 59%). 1H NMR (CDCl3, 400 MHz): δ=1.44-1.96 (m, 15H), 2.30 (s, 2H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated under vacuum
  4. customto give crude product, which
  5. customwas purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6ea67caa19ef43d084cf1bbdb95ce0e3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835426B2

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