Reaction #43551

Reaction equation

title compound

[1-(R)-Benzyloxymethyl-2-(5-fluoro-2,3-dihydro-indol-1-yl)-ethyl]-carbamic acid 1-(S)-cyclohexylmethyl-2-morpholin-4-yl-2-oxo-ethyl ester

→

title compound

Yield 71.4%

[2-(5-Fluoro-2,3-dihydro-indol-1-yl)-1-(R)-hydroxymethyl-ethyl]-carbamic acid 1-(S)-cyclohexylmethyl-2-morpholin-4-yl-2-oxo-ethyl ester

Yield 71.4%

Solvents

methanol

Conditions

Workup

1. 1
   OtherAir was purged from the reaction vessel and H2 gas
2. 2
   workup.ADDITIONwas introduced via a balloon
3. 3
   FiltrationThe Pd/C was filtered
4. 4
   Otherthe crude material was purified by reverse-phase HPLC

Procedure

The title compound of Example 10 (50 mg, 0.088 mmol) was dissolved in a minimum amount of methanol (approx. 1-2 mL) and a catalytic amount of 10% Pd/C was added. Air was purged from the reaction vessel and H2 gas was introduced via a balloon. The reaction mixture was stirred for several hours under a H2 atmosphere, after which point the starting material had disappeared by LCMS. The Pd/C was filtered and the crude material was purified by reverse-phase HPLC to afford the title compound (30 mg, 71% yield).

Source