Crotyl chloride → tert-Butyl 3-[(2E)-2-buten-1-yloxy]-4,4-dimethoxypiperidine-1-carboxylate

HRID 43682

Reaktionsgleichung

Reaktionsgleichung von HRID 43682
[OH:1][CH:2]1[C:7]([O:10][CH3:11])([O:8][CH3:9])[CH2:6][CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1.[H-].[Na+].[CH2:21](Cl)[CH:22]=[CH:23][CH3:24]>CN(C=O)C>[CH2:21]([O:1][CH:2]1[C:7]([O:8][CH3:9])([O:10][CH3:11])[CH2:6][CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1)/[CH:22]=[CH:23]/[CH3:24]

Komponenten

5

Edukt 3

HCID 11589Crotyl chlorideHCID 24758Sodium hydrideHCID 11425480Tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate

Produkt 1

HCID 67549820tert-Butyl 3-[(2E)-2-buten-1-yloxy]-4,4-dimethoxypiperidine-1-carboxylateAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The same operation as in Example (90a) was performed using tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate (5.2 g, 20 mmol), sodium hydride (55% content, 1.31 g, 30 mmol), crotyl chloride (3.63 g, 40 mmol) and DMF (50 mL). The residue was purified by column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1) to obtain 5.05 g of the title compound as a colorless oily substance (80%).

Aufarbeitung

  1. customThe residue was purified by column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1)

Quellen und Nachweise

ORD-Eintrag
ord-2e2e4c5beff2404d84b6ef85bbffd421
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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