Reaktion #93858

Reaktionsgleichung

2,2-dimethyl-1-(2-hydroxyethylidene)-7-methoxy-3-(N-methyl-p-toluenesulfonamido)1,2,3,4-tetrahydronaphthalene

sodium

hydrochloride

→

2,2-Dimethyl-1-(2-hydroxyethyl)-7-methoxy-3-methylamino-1,2,3,4-tetrahydronaphthalene hydrochloride

Lösungsmittel

ammonia

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigecan also be prepared
2. 2
   workup.ADDITIONIn this case again, a mixture of two stereoisomers
3. 3
   Sonstigeis obtained
4. 4
   Sonstigethe total yield

Vorschrift

This compound, described already in Examples 12 and 13, can also be prepared as described in Example 13, however, starting from 2,2-dimethyl-1-(2-hydroxyethylidene)-7-methoxy-3-(N-methyl-p-toluenesulfonamido)1,2,3,4-tetrahydronaphthalene. In this case, both the reduction of the olefinic double bond and the reductive cleavage of the p-toluenesulphonamido group are effectuated by the sodium metal dissolving in liquid ammonia. The endpoint of the reduction is reached if the blue colour persists for some 15 minutes. In this case again, a mixture of two stereoisomers is obtained, the total yield being 87% of crystalline hydrochloride.

Quelle