Reacción #1328402

Ecuación de reacción

N,N-dibenzyl-(1R,2S,4S)-1-methyl-2-hydroxy-4-phenylhexyl amine

acetic acid

→

(1R,2S,4S)-1-methyl-2-hydroxy-4-phenylhexyl amine

Rendimiento 78.5%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe catalyst was filtered off
2. 2
   OtroThe liquid filtrate thus obtained
3. 3
   Concentraciónwas concentrated under reduced pressure
4. 4
   workup.ADDITIONTo the resulting residue, a saturated sodium hydrogen carbonate aqueous solution (15 ml) was added
5. 5
   Extraccióntwo 50 ml methylene chloride extractions
6. 6
   SecadoThe resulting organic layer was dried with anhydrous magnesium sulfate
7. 7
   FiltraciónMagnesium sulfate was filtered off
8. 8
   Concentraciónthe liquid filtrate was concentrated under reduced pressure

Procedimiento

The N,N-dibenzyl-(1R,2S,4S)-1-methyl-2-hydroxy-4-phenylhexyl amine (1.46 g, 3.77 mmol) obtained above was dissolved in methanol (25 ml). Subsequently, acetic acid (0.43 ml, 7.53 mmol) and 5% Pd-C (palladium carbon; containing 50% of water) (0.6 g) were added to the dissolved solution. This reaction solution was stirred for 16 hours at 50° C. under a hydrogen atmosphere, and the catalyst was filtered off. The liquid filtrate thus obtained was concentrated under reduced pressure. To the resulting residue, a saturated sodium hydrogen carbonate aqueous solution (15 ml) was added and two 50 ml methylene chloride extractions were performed. The resulting organic layer was dried with anhydrous magnesium sulfate. Magnesium sulfate was filtered off and the liquid filtrate was concentrated under reduced pressure to yield (1R,2S,4S)-1-methyl-2-hydroxy-4-phenylhexyl amine (0.61 g, 2.96 mmol).

Fuente