Reaction #49172

Reaction equation

Compound 4a

(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid benzyl ester

→

compound 5

Yield 91.4%

6-Amino-1-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexan-1-one

Yield 91.4%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Otherpurged with argon
2. 2
   workup.ADDITIONTo the solution was added 10% palladium on carbon (2 g)
3. 3
   OtherThe flask was purged with hydrogen 2 times
4. 4
   FiltrationThe reaction mixture was filtered through a pad of Celite
5. 5
   Washwashed with ethyl acetate
6. 6
   ConcentrationThe combined organic layer was concentrated under reduced pressure

Procedure

Compound 4a (14.5 g, 21.7 mmol) was dissolved in ethyl acetate (100 mL) and purged with argon. To the solution was added 10% palladium on carbon (2 g). The flask was purged with hydrogen 2 times and stirred further at room temperature under hydrogen atmosphere for overnight. The disappearance of the starting material was confirmed by the TLC. The reaction mixture was filtered through a pad of Celite and washed with ethyl acetate. The combined organic layer was concentrated under reduced pressure to afford compound 5 (10.56 g, 91%) as white solid. This was used as such for the next step.

Source