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

HRID 2257975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2257975
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.[CH:20]1([CH2:25][C:26](O)=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21]1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH:20]1([CH2:25][C:26]([N:12]2[CH2:13][CH:14]3[C:17]([CH3:19])([CH3:18])[C@:10]([CH3:9])([CH2:16][CH2:15]3)[CH2:11]2)=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 71606Cyclopentylacetic acidHCID 22875699(1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride

Produkt 1

HCID 54371922(IS)-3-cyclopentylacetyl-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Triethylamine 0.43 ml was added in a methylene chloride 20 ml solution of (1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 0.49 g, and stirred at 0° C. for 45 min. Cyclopentyl acetic acid 0.36 ml and WSC 0.59 g were added therein, then the reaction mixture was gradually changed to room temperature and stirred for 24 hours. The reaction mixture was washed with 10% sodium hydroxide and dried by anhydrous sodium sulfate. After filtering the drying agent, the filtrate was concentrated in vacuo to obtain crude (IS)-3-cyclopentylacetyl-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 30 ml solution of lithium aluminum hydride 0.19 g and refluxed for 1.5 hours. The reaction mixture was cooled, then added ether, water and 10% aqueous sodium hydroxide thereto, and filtered the insoluble material. The filtrate was extracted with ether and dried by anhydrous sodium sulfate. After filtering the drying agent, a residue obtained by concentrating the filtrate in vacuo was purified by means of flash column chromatography (Merck, silica gel 60: 230-600 mesh, chloroform-chloroform:acetone=20:1) to obtain the product.

Aufarbeitung

  1. customwas gradually changed to room temperature
  2. stirringstirred for 24 hours
  3. washThe reaction mixture was washed with 10% sodium hydroxide
  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-a0b79ba00f544a17b849e86c3d6fe2d8
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05658923

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