Reaktion #527702

Reaktionsgleichung

water

triethylamine

Decanoyl chloride

(+)-1-[1-(2-chlorophenyl)cyclobutyl]-6-fluoro-7-hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide

→

(-)-1-[1-(2-chlorophenyl)cyclobutyl]-7-decanoyloxy-6-fluoro-2-methyl-1,2,3,4-tetrahydroisoquinoline

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared in a similar manner to that
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITcontinued for 1 hour
4. 4
   WaschenThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
5. 5
   Trocknendried over magnesium sulphate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo

Vorschrift

Decanoyl chloride (0.66 g) in dichloromethane (5 ml) was added to a stirring mixture of (+)-1-[1-(2-chlorophenyl)cyclobutyl]-6-fluoro-7-hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (1.5 g, prepared in a similar manner to that described in Example 64), triethylamine (1.06 g) and dichloromethane (25 ml). The mixture was stirred at ambient temperature for 20 minutes, then water (20 ml) was added and stirring continued for 1 hour. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine, then dried over magnesium sulphate, filtered and concentrated in vacuo to yield (-)-1-[1-(2-chlorophenyl)cyclobutyl]-7-decanoyloxy-6-fluoro-2-methyl-1,2,3,4-tetrahydroisoquinoline (1.31 g). This had a specific optical rotation αD of -5.59°.

Quelle