Reaktion #527701

Reaktionsgleichung

Decanoyl chloride

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

triethylamine

→

(+)-1-[1-(2-chlorophenyl)cyclopropyl]-7-decanoyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared in a similar manner to that
2. 2
   Waschenwashed with water, 10% aqueous sodium hydroxide solution, and brine
3. 3
   TrocknenThe organic layer was dried over magnesium sulphate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto yield a gum which
7. 7
   Sonstigewas purified by chromatography on a silica gel column
8. 8
   workup.ADDITIONa 1:3 mixture of ether and light petroleum as eluant
9. 9
   EinengenThe relevant fractions were concentrated in vacuo

Vorschrift

Decanoyl chloride (0.45 g) was added to a mixture of (+)-1-[1-(2-chlorophenyl)cyclopropyl]-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (1 g, prepared in a similar manner to that described in Example 77), triethylamine (0.7 g) and ether (30 ml). The mixture was stirred at ambient temperature for 24 hours, then washed with water, 10% aqueous sodium hydroxide solution, and brine. The organic layer was dried over magnesium sulphate, filtered and concentrated to yield a gum which was purified by chromatography on a silica gel column using a 1:3 mixture of ether and light petroleum as eluant. The relevant fractions were concentrated in vacuo to yield (+)-1-[1-(2-chlorophenyl)cyclopropyl]-7-decanoyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (0.95 g) as a gum; having specific optical rotation αD of +21.47°.

Quelle