2,3-Dihydroxy-4-methoxybenzoic acid → 7-Methoxy-1'-acetyl-spiro[1,3-benzodioxole-2,4'-piperidine]-4-carboxylic acid

HRID 2196093

Reaktionsgleichung

Reaktionsgleichung von HRID 2196093
[OH:1][C:2]1[C:10]([OH:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14]([N:17]1[CH2:22][CH2:21][C:20](OC)(OC)[CH2:19][CH2:18]1)(=[O:16])[CH3:15].C(N1CC=C(OC)CC1)(=O)C>>[CH3:13][O:12][C:9]1[C:10]2[O:11][C:20]3([O:1][C:2]=2[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=1)[CH2:21][CH2:22][N:17]([C:14](=[O:16])[CH3:15])[CH2:18][CH2:19]3

Komponenten

4

Edukt 3

HCID 775342,3-Dihydroxy-4-methoxybenzoic acidHCID 126536461-Acetyl-4,4-dimethoxy-piperidineHCID 187992181-Acetyl-4-methoxy-1,2,3,6-tetrahydropyridine

Produkt 1

HCID 592867277-Methoxy-1'-acetyl-spiro[1,3-benzodioxole-2,4'-piperidine]-4-carboxylic acidAusbeute 26,3 %

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 2,3-dihydroxy-4-methoxybenzoic acid (1.23 g, 6.67 mmol), 1-acetyl-4,4-dimethoxy-piperidine (1.4 g, 7.6 mmol) and 1-acetyl-1,2,3,6-tetrahydro-4-methoxy-pyridine (14.2 g, 91.5 mmol) was exposed to microwave heating (180° C., one hour) in a sealed reaction vessel. Filtration and subsequent standard HPLC purification afforded compound 508 (0.54 g, 26%). LC/MS (METHOD B): (m/z) 308.2 (MH+); RT=2.27 min; purity (UV)=95%.

Aufarbeitung

  1. customin a sealed reaction vessel
  2. filtrationFiltration and subsequent standard HPLC purification

Quellen und Nachweise

ORD-Eintrag
ord-e9fd4a743a404e43a1011bb7e10de4ca
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338431B2

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