Reaktion #89720

Reaktionsgleichung

methylene chloride

N,N-diisopropylethylamine

methyl chloroformate

(2S,3S,5R)-5-hydroxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid

1-phenyl-piperazine

benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate

N,N-dimethylformamide

N,N-diisopropylethylamine

→

titled compound

Ausbeute 83.0%

dimethyl(2S,3S,5R)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Ausbeute 83.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to 0 Celsius
2. 2
   workup.STIRRINGThe mixture was stirred at rt for 2 h
3. 3
   Einengenconcentrated
4. 4
   Sonstigeto dry
5. 5
   workup.ADDITIONThe residue was diluted with water
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   WaschenThe combined organic layers were washed with brine
8. 8
   Sonstigedried
9. 9
   Einengenconcentrated
10. 10
    Sonstigeto dry
11. 11
    SonstigeThe residue was purified on silica gel
12. 12
    Wascheneluting with 0 to 100% EtOAc in hexane

Vorschrift

To a mixture of (2S,3S,5R)-5-hydroxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid (3.140 g, 0.01545 mol), 1-phenyl-piperazine (2.597 mL, 0.01700 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (7.518 g, 0.01700 mol) in N,N-dimethylformamide (10.00 mL, 0.1291 mol) was added N,N-diisopropylethylamine (3.230 mL, 0.01854 mol) at 0 Celsius. After stirred at rt overnight. the reaction mixture was diluted with methylene chloride (90.0 mL, 1.40 mol) and then cooled to 0 Celsius. To the mixture was added N,N-diisopropylethylamine (5.38 mL, 0.0309 mol) followed by methyl chloroformate (2.39 mL, 0.0309 mol). The mixture was stirred at rt for 2 h and then concentrated to dry. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated to dry. The residue was purified on silica gel, eluting with 0 to 100% EtOAc in hexane, to give The titled compound (5.20 g, 83.0%). MS (ESI): (M+H)+=406.1.

Quelle