Methyl 6-chloro-5-nitronicotinate → (S)-Methyl 6-(2-(methoxycarbonyl)pyrrolidin-1-yl)-5-nitronicotinate

HRID 716206

Reaktionsgleichung

Reaktionsgleichung von HRID 716206
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([O:8][CH3:9])=[O:7].Cl[C:11]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1>CCOC(C)=O>[CH3:9][O:8][C:6]([C@@H:2]1[CH2:3][CH2:4][CH2:5][N:1]1[C:11]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1)=[O:7]

Komponenten

4

Edukt 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 853477Methyl L-prolinate

Produkt 1

HCID 58324504(S)-Methyl 6-(2-(methoxycarbonyl)pyrrolidin-1-yl)-5-nitronicotinateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(S)-Methyl pyrrolidine-2-carboxylate (6.56 g, 50.8 mmol) was added to methyl 6-chloro-5-nitronicotinate (5.00 g, 23.1 mmol) and the reaction mixture was stirred at 90° C. for 10 min (exothermic reaction). It as cooled to room temperature, diluted with EtOAc (10 mL) and purified using flash column chromatography on silica gel (20-30% EtOAc in hexanes) to afford the title compound as a yellow oil (6.70 g, 94%). [M+H] calc'd for C13H15N3O6, 310. found, 310.

Aufarbeitung

  1. custom(exothermic reaction)
  2. temperatureIt as cooled to room temperature
  3. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-b6d0d4096b8f4ffda1aa76a9db4c39be
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187497B2

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