Iodocyclopentane → 5-Cyano-5-cyclopentyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide

HRID 1873541

Reaktionsgleichung

Reaktionsgleichung von HRID 1873541
[CH3:1][N:2]([CH3:15])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][CH:11]([C:13]#[N:14])[CH2:12][CH:7]2[CH2:6]1)=[O:4].I[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>CN(C)C=O.O>[CH3:1][N:2]([CH3:15])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([C:13]#[N:14])([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:12][CH:7]2[CH2:6]1)=[O:4]

Komponenten

6

Edukt 3

HCID 73784IodocyclopentaneHCID 2733832Lithium HexamethyldisilazideHCID 686261915-Cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide

Produkt 1

HCID 686258275-Cyano-5-cyclopentyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 12a was dissolved in 30 mL of N,N-dimethylformamide followed by addition of iodo-cyclopentane (5.4 g, 27.5 mmol) and lithium hexamethyldisilazide (27.5 mL, 27.5 mmol) under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was diluted with 10 mL of water and concentrated to remove N,N-dimethylformamide and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-cyano-5-cyclopentyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 16a (2.6 g, yield 42%) as a light yellow solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customto remove N,N-dimethylformamide
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3cc2244656264d7a8c24fac657b8f5cf
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304411B2

Verknüpfte Notizen

Wird geladen…