Ammonia → 3-cyclopropylmethyl 5-[2-(N-methyl-N-trimethylsilylmethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 621541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 621541
[C:1]([O:7][CH2:8][CH2:9][N:10]([CH3:16])[CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:17]([C:20]1[CH:21]=[C:22]([CH:35]=[CH:36][CH:37]=1)[CH:23]=[C:24]([C:32]([CH3:34])=O)[C:25]([O:27][CH2:28][CH:29]1[CH2:31][CH2:30]1)=[O:26])([O-:19])=[O:18].[NH3:38]>C(O)C>[CH3:34][C:32]1[NH:38][C:3]([CH3:5])=[C:2]([C:1]([O:7][CH2:8][CH2:9][N:10]([CH3:16])[CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[O:6])[CH:23]([C:22]2[CH:35]=[CH:36][CH:37]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=2)[C:24]=1[C:25]([O:27][CH2:28][CH:29]1[CH2:31][CH2:30]1)=[O:26]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 212433402-(N-methyl-N-trimethylsilylmethylamino)ethyl acetoacetateHCID 53956239Cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate

Produkt 1

HCID 141000963-cyclopropylmethyl 5-[2-(N-methyl-N-trimethylsilylmethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylateAusbeute 25,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 15.3 g (53 mmol) of 2-(N-methyl-N-trimethylsilylmethylamino)ethyl acetoacetate, 13.0 g (53 mmol) of cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate, 4.4 ml of 28% aqueous ammonia and 50 ml of ethanol was stirred at the reflux temperature for 7 hours, and then the solvent was removed under reduced pressure. The residue was chromatographed on silica gel column to afford 3-cyclopropylmethyl 5-[2-(N-methyl-N-trimethylsilylmethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (7.0 g, 25.7%) as yellow oil. Treatment of this oil with 1 equivalent of fumaric acid in ethanol gave the corresponding fumarate.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-c949359ff57f46b29008d9dee23b3171
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04824855

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