Ethyl Acetoacetate → HCID 59376005, Verbindung

HRID 661487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661487
N1C2CCCC(=O)C=2C=C1.C(OCC)(=O)CC(C)=O.P([O-])(O)(O)=O.[Na+].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:40][C:41]1[NH:42][C:43]2[C:44](=[O:55])[CH2:45][CH2:46][CH2:47][C:48]=2[C:49]=1[C:50]([O:52]CC)=[O:51]>>[CH3:40][C:41]1[NH:42][C:43]2[C:44](=[O:55])[CH2:45][CH2:46][CH2:47][C:48]=2[C:49]=1[C:50]([OH:52])=[O:51]

Komponenten

6

Edukt 5

HCID 8868Ethyl AcetoacetateHCID 14812Phosphorus oxide (P4O10)HCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 23672064Monosodium phosphateHCID 59376018ethyl 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate

Produkt 1

HCID 59376005HCID 59376005, Verbindung

Versuchsvorschrift

In one more aspect, the present invention relates to pyrrolo[b]cyclohexanone, the intermediate of Formula (II), which is synthesized by the route outlined below: 6-amino-5-oxohexanoic acid hydrochloride(S1) and ethyl acetoacetate were refluxed in a.q. sodium dihydrogen phosphate to generate substituted pyrrole(S2). Then the compound S2 was solved in polyphosphoric acid (PPA), P2O5 used as dehydrant, reacted to generate ethyl 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate (S3) at 70° C. 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (S4) is obtained by the hydrolysis of (S3) in 1 mol/L a.q. LiOH. Finally, S4 is reacted with H—R6 at room temperature for 24 hours in DMF to give pyrrolo[b]cyclohexanone of Formula (II) by using a condensation reagent.

Aufarbeitung

  1. temperaturewere refluxed in a.q
  2. customreacted
  3. customat 70° C

Quellen und Nachweise

ORD-Eintrag
ord-30cdfd34733a40c6b35131191a3d4dc2
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084621B2

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