Dimethyl 3-oxoglutarate → Methyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

HRID 910143

Reaktionsgleichung

Reaktionsgleichung von HRID 910143
CO[C:3]([CH2:5][C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:7])=[O:4].CO[C:15]1[CH2:16][CH2:17][CH2:18][N:19]=1>C(N(CC)CC)C>[OH:7][C:6]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:18]2[N:19]([CH2:15][CH2:16][CH2:17]2)[C:3](=[O:4])[CH:5]=1

Komponenten

4

Edukt 2

HCID 74591Dimethyl 3-oxoglutarateHCID 3534432-Methoxy-1-Pyrroline

Produkt 1

HCID 54694252Methyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineKatalysator

Versuchsvorschrift

Triethylamine (0.5 mL, 3.6 mmol) was added to a mixture of dimethyl 1,3-acetonedicarboxylate (16.3 mL, 111 mmol) and 5-methoxy-3,4-dihydro-2H-pyrrole (10 g, 101 mmol), and the reaction stirred for 72 h. The white solid was collected by filtration, rinsed with ether, and dried under vacuum to give 15.8 g (75%) of compound 1a. 1H NMR (400 MHz, DMSO-d6): δ 11.11 (s, 1H), 5.54 (s, 1H), 3.94 (t, 2H, J=7.6 Hz), 3.80 (s, 3H), 3.36 (t, 2H, J=7.6 Hz), 2.02-2.11 (m, 2H). MS (ES) [m+H] calc'd for C10H11NO4, 210. found 210.

Aufarbeitung

  1. filtrationThe white solid was collected by filtration
  2. washrinsed with ether
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-459e70a3e1d7495082c1a00c4f4d7a75
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022057B2

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