Sodium hydride → Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate

HRID 531463

Reaktionsgleichung

Reaktionsgleichung von HRID 531463
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[CH:3]=1.P(OCC)(OCC)OCC.O=[C:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.[H-].[Na+]>O.COCCOC>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:8]=[C:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 31215Triethyl phosphiteHCID 699793-Bromobenzyl bromideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Produkt 1

HCID 57813409Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylateAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

The mixture of 1-bromo-3-(bromomethyl)benzene (6.2 g, 24.8 mmol) and triethyl phosphite (4.53 g, 27.28 mmol) was heated at 90° C. for 12 hours, cooled to 0° C., added DME (40 ml) and tert-butyl 4-oxopiperidine-1-carboxylate (5.73 g, 28.8 mmol) and sodium hydride (1.19 g, 49.6 mmol) and stirred at RT for 2-3 hours. Diluted with water and extracted with ether to afford 4.5 g (51.5% yield) of the titled product after purification with (60/120 silica gel) column chromatography using 10% ethyl acetate in hexane as eluent. MS: m/z=353.2 (M+1).

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. extractionextracted with ether

Quellen und Nachweise

ORD-Eintrag
ord-7449a3134678448683907a8a825d8072
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353107B2

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