Reaction #1328402

Reaction equation

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

Yield 78.5%

Solvents

methanol

Conditions

Workup

1. 1
   Filtrationthe catalyst was filtered off
2. 2
   OtherThe liquid filtrate thus obtained
3. 3
   Concentrationwas concentrated under reduced pressure
4. 4
   workup.ADDITIONTo the resulting residue, a saturated sodium hydrogen carbonate aqueous solution (15 ml) was added
5. 5
   Extractiontwo 50 ml methylene chloride extractions
6. 6
   DryingThe resulting organic layer was dried with anhydrous magnesium sulfate
7. 7
   FiltrationMagnesium sulfate was filtered off
8. 8
   Concentrationthe liquid filtrate was concentrated under reduced pressure

Procedure

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).

Source