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

HRID 2097823

Reaktionsgleichung

Reaktionsgleichung von HRID 2097823
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[C:21]([O:23][CH3:24])=[O:22]>C(OCC)(=O)C>[CH3:24][O:23][C:21]([C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:15]1[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1)=[O:22]

Komponenten

4

Edukt 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 853680(S)-Methyl piperidine-2-carboxylate

Produkt 1

HCID 58324510(S)-methyl 6-(2-(methoxycarbonyl)piperidin-1-yl)-5-nitronicotinateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 6-chloro-5-nitronicotinate (2.333 g, 10.77 mmol) was added to (S)-methyl piperidine-2-carboxylate (2.93 g, 20.46 mmol) neat while stirring. The reaction was stirred 1 h at 90° C., cooled to room temperature and taken up in ethyl acetate (10 mL). The mixture was purified by SiO2 (330 g, 20-30% EA in Hexanes) to yield 3.4 g (98%) of the title compound as a yellow oil. [M+H] calc'd for C, 14; H, 17; N, 3; O, 6, 324; found, 324.

Aufarbeitung

  1. stirringThe reaction was stirred 1 h at 90° C.
  2. customThe mixture was purified by SiO2 (330 g, 20-30% EA in Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-876f4f765eca45afb0e53eec788b84c5
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450323B2

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