Reaktion #499703

Reaktionsgleichung

water

chloromethyl methyl sulfide

7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

sodium hydride

→

title compound

7-Methylthiomethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic Acid tert-Butyl Ester

Lösungsmittel

dirnethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature overnight
3. 3
   SonstigeAfter completion of the reaction
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   Waschenwashed successively with water and saturated brine
6. 6
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
7. 7
   Sonstigethe solvent was evaporated
8. 8
   Sonstigethe obtained residue was purified by silica gel column chromatography (hexane:acetone=20:1-10:1)
9. 9
   Sonstigedried under reduced pressure

Vorschrift

To a solution of 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester (13 g) in dirnethylformamide (100 ml) was added 60% sodium hydride (2.5 g) under an argon atmosphere, and the mixture was stirred at room temperature for 30 minutes. Then, chloromethyl methyl sulfide (5.2 ml) was dropwise added with ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:acetone=20:1-10:1) and dried under reduced pressure to give the title compound (9.6 g).

Quelle