Tricyclo(3.3.1.13,7)dec-1-ylmethylamine → N-(1-adamantylmethyl)-5-methyl-3-oxohexanamide

HRID 75154

Reaktionsgleichung

Reaktionsgleichung von HRID 75154
[CH3:1][CH:2]([CH3:16])[CH2:3][C:4]([CH:6]1[C:11](=[O:12])OC(C)(C)OC1=O)=[O:5].[C:17]12([CH2:27][NH2:28])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2>O1CCOCC1>[C:17]12([CH2:27][NH:28][C:11](=[O:12])[CH2:6][C:4](=[O:5])[CH2:3][CH:2]([CH3:1])[CH3:16])[CH2:24][CH:23]3[CH2:22][CH:21]([CH2:20][CH:19]([CH2:25]3)[CH2:18]1)[CH2:26]2

Komponenten

4

Edukt 2

HCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 594371732,2-Dimethyl-5-(3-methylbutanoyl)-1,3-dioxane-4,6-dione

Produkt 1

HCID 59437162N-(1-adamantylmethyl)-5-methyl-3-oxohexanamideAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 5-(3-methylbutanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (2.76 g, 12 mmol) and (1-adamantylmethyl)amine (2 g, 12 mmol) in anhydrous 1,4-dioxane (10 mL) was heated under reflux for 2 h. Solvent was removed in vacuo. The residue was diluted with EtOAc (50 mL), washed with water, aq K2CO3 and brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by chromatography on a silica gel column eluted with 20:1 PE/EtOAc to give the N-(1-adamantylmethyl)-5-methyl-3-oxohexanamide (1.90 g, 54.4%). 1H NMR: (400 MHz, CDCl3): δ=0.92 (s, 3H), 0.96 (s, 3H), 1.54 (s, 7H), 1.62-1.73 (m, 9H), 1.98 (s, 4H), 2.12(m, 1H), 2.45(d, 2H), 2.95(d, 2H), 3.65(s, 2H).

Aufarbeitung

  1. temperatureunder reflux for 2 h
  2. customSolvent was removed in vacuo
  3. additionThe residue was diluted with EtOAc (50 mL)
  4. washwashed with water, aq K2CO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by chromatography on a silica gel column
  8. washeluted with 20:1 PE/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-0ecc176c213940abade3d063b7446509
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835426B2

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