(S)-4-[(E)-2-(6-chloro-pyridin-3-yl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester → (S)-4-[2-(6-chloro-pyridin-3-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1187778

Reaktionsgleichung

Reaktionsgleichung von HRID 1187778
[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[CH:14]/[C:15]2[CH:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pt]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 86664598(S)-4-[(E)-2-(6-chloro-pyridin-3-yl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Produkt 1

HCID 86664597(S)-4-[2-(6-chloro-pyridin-3-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl esterAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred suspension of (S)-4-[(E)-2-(6-chloro-pyridin-3-yl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.0 g) in methanol (70 ml) was added platinum on charcoal (0.58 g, 10 wt %) and the mixture was stirred under an atmosphere of hydrogen at room temperature for 15 min. The mixture was then filtered through celite and the filtrate was concentrated in vacuo to give (S)-4-[2-(6-chloro-pyridin-3-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (949 mg, 94%) as a colourless oil. MS (ISP): 343.2 ([{37Cl}M+H]+), 341.1 ([{35Cl}M+H]+), 287.0 ([{37Cl}M+H—C4H8]+), 285.1 ([{35Cl}M+H—C4H8]+).

Aufarbeitung

  1. filtrationThe mixture was then filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e2dec380e5c843d6bdc4cc29bb60b0d4
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673950B2

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