Reaktion #89745

Reaktionsgleichung

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

triethylamine

methylene chloride

methanesulfonyl chloride

→

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

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter quenched with MeOH
2. 2
   Sonstigethe mixture was evaporated
3. 3
   Sonstigeto dry in vacuo
4. 4
   workup.ADDITIONdiluted with ethyl acetate
5. 5
   WaschenThe organic layers were washed with water, brine
6. 6
   Sonstigedried
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto dry
9. 9
   SonstigeThe residue was purified on silica gel
10. 10
    Wascheneluting with 0 to 80% EtOAc in hexane

Vorschrift

To a stirred solution of dimethyl(2S,3S,5R)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate (1.00 g, 0.00247 mol) and triethylamine (0.412 mL, 0.00296 mol) in methylene chloride (20.00 mL, 0.3120 mol) was added methanesulfonyl chloride (0.210 mL, 0.00271 mol). The mixture was stirred at rt overnight. After quenched with MeOH, the mixture was evaporated to dry in vacuo and diluted with ethyl acetate. The organic layers were washed with water, brine and dried, concentrated to dry. The residue was purified on silica gel, eluting with 0 to 80% EtOAc in hexane, to generate the mesylate compound (0.98 g, 82%). MS (ESI): (M+H)+=484.1.

Quelle