Reaktion #324912

Reaktionsgleichung

sodium hydrogen cyanamide

(S)-2-(4-tert-butylphenoxymethyl)-oxirane

→

(S)-5-(4-tert-butyl-phenoxymethyl)-(4,5-dihydro-oxazol-2-yl)amine

Ausbeute 41.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenwas concentrated
2. 2
   Sonstigeto remove methanol
3. 3
   workup.ADDITIONAnhydrous diethyl ether (150 mL) was added
4. 4
   FiltrationThe resulting white precipitate was filtered through celite
5. 5
   Einengenthe filtrate was concentrated
6. 6
   SonstigeThe residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride)

Vorschrift

To a vigorously stirred solution of sodium hydrogen cyanamide (2.92 g, 44.5 mmol) in methanol (40 mL) was added dropwise (S)-2-(4-tert-butylphenoxymethyl)-oxirane (9.18 g, 44.5 mmol). The reaction mixture was stirred at room temperature overnight after which the reaction mixture was concentrated to remove methanol. Anhydrous diethyl ether (150 mL) was added. The resulting white precipitate was filtered through celite and the filtrate was concentrated. The residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride) to give 4.53 g (41%) of (S)-5-(4-tert-butyl-phenoxymethyl)-(4,5-dihydro-oxazol-2-yl)amine.

Quelle