Reaktion #55457

Reaktionsgleichung

lithium aluminum hydride

2-(1-benzyl-5-methyl-4-imidazolyl)-1,3-dithian-5-one oxime

water

→

Trans 2-(1-benzyl-5-methyl-4-imidazolyl)-5-amino-1,3-dithiane

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe mixture is filtered hot
2. 2
   SonstigeThe solvent is evaporated
3. 3
   Sonstigeto remove traces of water
4. 4
   Sonstigeto give a viscous oil (17.0 g.)
5. 5
   WaschenCareful chromatography on silica gel by gradient elution with 2-6% methanol/chloroform
6. 6
   Sonstigeaffords 2.2 g

Vorschrift

To a suspension of lithium aluminum hydride (2.9 g., 0.076 mole) in dry tetrahydrofuran (120 ml.) under a nitrogen atmosphere is added dropwise a solution of 2-(1-benzyl-5-methyl-4-imidazolyl)-1,3-dithian-5-one oxime (21.3 g., 0.0668 mole) in dry tetrahydrofuran (130 ml.). After heating at 70° C. for one hour, water (40 ml.) is added cautiously and the mixture is filtered hot. The solvent is evaporated and the residue is chased with ethanol to remove traces of water to give a viscous oil (17.0 g.). Careful chromatography on silica gel by gradient elution with 2-6% methanol/chloroform affords 2.2 g. of the trans isomer and 7.3 g. of the cis isomer as viscous semi-solids.

Quelle