Triethylamine → Ethyl 3-methyl-2,4,5,6-tetrahydrocyclopenta[c]pyrrole-1-carboxylate

HRID 1757589

Reaktionsgleichung

Reaktionsgleichung von HRID 1757589
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[C:16]([CH:19]1[CH2:23][CH2:22][CH2:21][C:20]1=O)(=O)[CH3:17].[O-]CC.[Na+]>C(O)C.O>[CH3:17][C:16]1[NH:2][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:20]2[CH2:21][CH2:22][CH2:23][C:19]=12

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 984712-AcetylcyclopentanoneHCID 2723640Glycine ethyl ester, hydrochlorideHCID 2723922Sodium ethoxide

Produkt 1

HCID 13863058Ethyl 3-methyl-2,4,5,6-tetrahydrocyclopenta[c]pyrrole-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A procedure for the synthesis of pyrroles via N-(3-oxo-1-alkenyl)glycine ester was adapted from Hombrecher and Horter, Synthesis 389, 1990. Ethyl aminoacetate hydrochloride (28 g, 0.20 mol) and triethylamine (20.1 g, 0.20 mol) were added to a solution of 2-acetylcyclopentanone (25.0 g, 0.20mol) in ethanol (400 ml). The solution was stirred at room temperature for 15 hours and concentrated. The residue was combined with water (250 ml), and extracted with methylene chloride (4×100 ml). The combined extract was washed with water (100 ml), dried (sodium sulfate), and concentrated to leave a light brown oil. The oil was added with stirring at 50° C. to a solution of sodium ethoxide (14 g, 0.20 mol) in absolute ethanol (400 ml). The mixture was heated at 80° C. for 3 hours and poured into water (500 ml) to precipitate a light yellow solid. Recrystallization from ethanol gave ethyl 3-methyl-2,4,5,6-tetrahydrocyclopenta[c]pyrrolecarboxylate 4j, 9.1 g (24%)as a pale yellow solid, mp 166°-167° C.; 1H NMR (CDCl3): δ 8.38 (s, 1H), 4.24 (q, 2H), 2.78 (t, 2H), 2.52 (t, 2H), 2.30 (m, 2H), 2.18 (s, 3H), 1.30 (t, 3H). Anal. calcd for C11H15NO2 : C, 68.39; H, 7.77; N, 7.25. Found, C, 68.40; H, 7.85; N, 7.15.

Aufarbeitung

  1. customwas adapted from Hombrecher and Horter, Synthesis 389, 1990
  2. concentrationconcentrated
  3. extractionextracted with methylene chloride (4×100 ml)
  4. extractionThe combined extract
  5. washwas washed with water (100 ml)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customto leave a light brown oil
  9. additionThe oil was added
  10. temperatureThe mixture was heated at 80° C. for 3 hours
  11. customto precipitate a light yellow solid
  12. customRecrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-1352f590c1a6406cb9093c7128fea9b7
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05446157

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