Reaction #586113

Reaction equation

N-{(S)-1-hydroxy-3-phenyl-2-propyl}-5-benzyloxy-2-hydroxybenzamide

→

N-{(S)-1-hydroxy-3-phenyl-2-propyl }-2,5-dihydroxybenzamide

Yield 85.0%

Solvents

methanol

Conditions

Workup

1. 1
   OtherIn a flask equipped with a magnetic stirring bar
2. 2
   OtherNitrogen is bubbled through the solution and 10% Pd on charcoal
3. 3
   workup.ADDITIONis added
4. 4
   OtherAfter flushing with nitrogen
5. 5
   OtherThe suspension is flushed with nitrogen
6. 6
   Filtrationfiltered
7. 7
   Washrinsed over Celite
8. 8
   ConcentrationThe filtrate is concentrated under vacuum

Procedure

In a flask equipped with a magnetic stirring bar and a rubber septum is dissolved the N-{(S)-1-hydroxy-3-phenyl-2-propyl}-5-benzyloxy-2-hydroxybenzamide in methanol. Nitrogen is bubbled through the solution and 10% Pd on charcoal is added. After flushing with nitrogen, the suspension is placed under hydrogen atmosphere and stirred for 2 hours. The suspension is flushed with nitrogen and filtered and rinsed over Celite. The filtrate is concentrated under vacuum. In this fashion is obtained N-{(S)-1-hydroxy-3-phenyl-2-propyl }-2,5-dihydroxybenzamide (85%).

Source