Reaktion #334644

Reaktionsgleichung

sodium borohydride

2-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene hydrochloride

sodium borohydride

phenylglyoxal

water

→

2-[(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-phenylethanol hydrochloride

Ausbeute 20.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe reacting mixture is left
2. 2
   workup.STIRRINGthe solution is stirred at room temperature for 15 minutes
3. 3
   Sonstigeit is evaporated to dryness
4. 4
   workup.DISSOLUTIONThe residue is dissolved in 300 ml of ethyl acetate
5. 5
   Filtrationafter filtration
6. 6
   Sonstigethe organic phase is separated
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated to dryness
10. 10
    SonstigeThe oil thus obtained
11. 11
    Sonstigeis purified by flash-chromatography

Vorschrift

An amount of 3.53 g of phenylglyoxal is reacted under stirring at room temperature for 3 hours with 5 g of 2-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene hydrochloride in 100 ml of methanol in the presence of 0.9 g of sodium borohydride. After cooling to 4° C., 4,3 g of sodium borohydride are added and the reacting mixture is left under stirring at room temperature for a night. After addition of 20 ml of water, the solution is stirred at room temperature for 15 minutes, then it is evaporated to dryness. The residue is dissolved in 300 ml of ethyl acetate and 60 ml of water; after filtration, the organic phase is separated, dried over magnesium sulfate, filtered and evaporated to dryness. The oil thus obtained is purified by flash-chromatography by using a mixture ethyl acetate/methanol 8/2 as eluant to obtain the 2-[(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-phenylethanol hydrochloride. Yield: 20% of the theoretical value.

Quelle