Triethylamine → (IS)-3-(1-adamantyl carbonyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

HRID 2257982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2257982
C(N(CC)CC)C.Cl.[CH3:9][C@@:10]12[C:17]([CH3:19])([CH3:18])[CH:14]([CH2:15][CH2:16]1)[CH2:13][NH:12][CH2:11]2.CCN=C=NCCCN(C)C.[C:31]12([C:41](O)=[O:42])[CH2:40][CH:35]3[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]3)[CH2:32]1)[CH2:38]2>C(Cl)Cl>[C:31]12([C:41]([N:12]3[CH2:13][CH:14]4[C:17]([CH3:19])([CH3:18])[C@:10]([CH3:9])([CH2:16][CH2:15]4)[CH2:11]3)=[O:42])[CH2:38][CH:37]3[CH2:36][CH:35]([CH2:34][CH:33]([CH2:39]3)[CH2:32]1)[CH2:40]2

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 132351-Adamantanecarboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22875699(1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride

Produkt 1

HCID 53642902(IS)-3-(1-adamantyl carbonyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Triethylamine 0.096 ml was added in a methylene chloride 5 ml solution of (IS)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 100 mg, and stirred at 0° C. for 30 min. WSC 0.13 g and 1-adamantanecarboxylic acid 0.11 g were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 15 hours. The reaction mixture was washed with saturated sodium chloride solution and dried by anhydrous sodium sulfate. After filtering the drying agent, the filtrate was concentrated in vacuo to obtain crude (IS)-3-(1-adamantyl carbonyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 10 ml solution of lithium aluminum hydride 24.0 mg and refluxed under heating for 1.5 hour. The reaction mixture was cooled, then added water, and removed the insoluble material by filtration. The filtrate was concentrated in vacuo. The thus obtained residue was purified by means of silica gel column chromatography (Wako gel, C200, chloroform) to obtain the product.

Aufarbeitung

  1. customwas gradually changed to room temperature
  2. stirringstirred for 15 hours
  3. washThe reaction mixture was washed with saturated sodium chloride solution
  4. dry with materialdried by anhydrous sodium sulfate
  5. filtrationAfter filtering the drying agent
  6. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-242f00601105478e86b6adced0c8b50c
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05658923

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