Reaktion #2349674

Reaktionsgleichung

(R)-(4-Methyl-morpholin-2-yl)-methanol

Intermediate 11

(R)-(4-Methyl-morpholin-2-yl)-methanol

NaH

4-Nitrophenyl 4-phenylpiperazine-1-carboxylate

4-nitrophenyl 4-phenylpiperazine-1-carboxylate

Intermediate 2

4-nitrophenyl 4-phenylpiperazine-1-carboxylate

→

[(2R)-4-methylmorpholin-2-yl]methyl 4-phenylpiperazine-1-carboxylate

Ausbeute 72.1%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 48 h
2. 2
   FiltrationThe reaction mixture was filtered through celite
3. 3
   Waschenthe solid washed with THF (10 mL)
4. 4
   Sonstigethe solvent removed in vacuo
5. 5
   SonstigeThe residue was purified by column chromatography (normal phase silica, 5 g Isolute-Si column, gradient 1-5% MeOH in DCM)
6. 6
   SonstigeThe solvents were removed in vacuo

Vorschrift

(R)-(4-Methyl-morpholin-2-yl)-methanol (Intermediate 11; 100 mg, 0.76 mmol) was added to a suspension of NaH (60% dispersion in oil; 90.0 mg, 2.28 mmol) in anhydrous THF (7 mL) and stirred under nitrogen for 30 min. 4-Nitrophenyl 4-phenylpiperazine-1-carboxylate (Intermediate 2; 300 mg, 0.92 mmol) was added and the reaction mixture was stirred at room temperature for 48 h. The reaction mixture was filtered through celite and the solid washed with THF (10 mL). The filtrates were combined and the solvent removed in vacuo. The residue was purified by column chromatography (normal phase silica, 5 g Isolute-Si column, gradient 1-5% MeOH in DCM). The solvents were removed in vacuo to give [(2R)-4-methylmorpholin-2-yl]methyl 4-phenylpiperazine-1-carboxylate (175 mg, 72%) as a light yellow gum

Quelle