Reaktion #499712

Reaktionsgleichung

water

chloromethyl methyl sulfide

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

sodium hydride

→

title compound

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

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling and under an argon atmosphere
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 12 hours
3. 3
   workup.ADDITIONwas added
4. 4
   Extraktionthe mixture was extracted with ethyl acetate
5. 5
   Waschenwashed with water
6. 6
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
7. 7
   Sonstigethe solvent was evaporated
8. 8
   SonstigeThe obtained oil was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)
9. 9
   Sonstigedried under reduced pressure

Vorschrift

To a solution of 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester (2.5 g) in dimethylformamide (25 ml) was added 60% sodium hydride (390 mg) with ice-cooling and under an argon atmosphere, and the mixture was stirred at the same temperature for 30 min. Then, chloromethyl methyl sulfide (0.96 ml) was added, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained oil was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) and dried under reduced pressure to give the title compound (2.7 g).

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