Reaction #969888

Reaction equation

5-[1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-thiazolidine-2,4-dione

→

(5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione

Solvents

EtOH

MeOH

DCM

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONwas added to the reaction
3. 3
   workup.ADDITIONvial containing the catalyst solution
4. 4
   OtherThe vial was purged with N2 (5×) and H2 (5×)
5. 5
   workup.ADDITIONfinally charged with 25 bar of H2
6. 6
   Otherthe reaction
7. 7
   Othervial was purged with N2 (3×)
8. 8
   OtherA sample of the reaction

Procedure

A stock solution of the Rh(COD)2BF4 (10.6 mg, 26.1 μmol) in DCM (9.5 mL) was made in a glove box. Ligand SL-WO03-2 ((S)-1-[(S)-2-(2i -diphenylphosphinophenyl)ferrocenyl]ethyl-dicyclohexyl phosphine) (8.4 mg, 12.5 μmol), was weighed into a vial and 500 μL of the Rh(COD)2BF4 stock solution was added. A solution of 5-[1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-thiazolidine-2,4-dione (4.5 mL of a stock solution containing 78.2 mg in 35 mL MeOH) was added to the reaction vial containing the catalyst solution. The vial was purged with N2 (5×) and H2 (5×) and finally charged with 25 bar of H2. After 18 h the H2 was released and the reaction vial was purged with N2 (3×). A sample of the reaction vial was taken and diluted with an equal volume of EtOH containing 1% formic acid. e.e. (Method 4) 75%, Rt 36.11 min, conversion 50%.

Source