Reaktion #43301

Reaktionsgleichung

Methyliodide

water

Sodiumhydride

1,1-dimethylethyl trans-3-hydroxy-4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-piperidinecarboxylate

→

intermediate 45

1,1-dimethylethyl trans-4-[[[(4-methylphenyl)sulfonyl]oxy]-methyl]-3-methoxy-1-piperidinecarboxylate

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction under nitrogen atmosphere
2. 2
   Sonstigethe resulting reaction mixture
3. 3
   workup.STIRRINGwas stirred for 90 minutes
4. 4
   SonstigeThe solvent was evaporated
5. 5
   Sonstigethe residue was partitioned between water and DCM
6. 6
   SonstigeThe organic layer was separated
7. 7
   Sonstigedried
8. 8
   Filtrationfiltered
9. 9
   Sonstigethe solvent was evaporated

Vorschrift

Reaction under nitrogen atmosphere. Sodiumhydride (0.3 mol) was added to a solution of 1,1-dimethylethyl trans-3-hydroxy-4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-piperidinecarboxylate [described in WO-00/37461 as intermediate (1-c)] (0.27 mol) in THF (1300 ml). The mixture was stirred for 30 minutes. Methyliodide (0.54 mol) was added and the resulting reaction mixture was stirred for 90 minutes. A small amount of water was added. The solvent was evaporated and the residue was partitioned between water and DCM. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 1,1-dimethylethyl trans-4-[[[(4-methylphenyl)sulfonyl]oxy]-methyl]-3-methoxy-1-piperidinecarboxylate (intermediate 45).

Quelle