Sodium hydride → tert-Butyl 3-(2-fluoroethoxy)-4,4-dimethoxypiperidine-1-carboxylate

HRID 43696

Reaktionsgleichung

Reaktionsgleichung von HRID 43696
[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+].C1(C)C=CC(S(O[CH2:31][CH2:32][F:33])(=O)=O)=CC=1>CN(C=O)C>[F:33][CH2:32][CH2:31][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

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 11425480Tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate

Produkt 1

HCID 86648640tert-Butyl 3-(2-fluoroethoxy)-4,4-dimethoxypiperidine-1-carboxylateAusbeute 97,7 %

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 (6.2 g, 23.7 mmol), sodium hydride (55% content, 1.57 g, 36 mmol), 2-fluoroethyl p-toluenesulfonate (7.85 g, 46 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 7.12 g of the title compound as a colorless oily substance (98%).

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-157ef90c9b174bd2b69c67455a7bca91
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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