tert-butyl (R)-3-(hydroxymethyl)hexanoate Chemical Properties

Boiling point:

278.5±23.0 °C(Predicted)

Density 

0.956±0.06 g/cm3(Predicted)

pka

14.78±0.10(Predicted)

tert-butyl (R)-3-(hydroxymethyl)hexanoate Usage And Synthesis

Uses

Tert-butyl (R)-3-(hydroxymethyl)hexanoate is employed in the biocatalytic route to the novel antiepileptic drug brivaracetam.

Synthesis

Sodium borohydride was slowly added to pre-cooled tetrahydrofuran at -5-0°C and stirred for 5 min. BF3-etherate (25.6 g) was slowly added to the reaction mixture at -5-0°C and stirred for 15 min at the same temperature. (R)-2-(2-(tert-butoxy)-2-oxoethyl)pentanoic acid (23 g) was added to the reaction mixture and stirred for 3 h. The reaction mixture was slowly quenched with water and raised the temperature of the reaction mixture to 25-30°C. Separated both the aqueous and organic layers and the aqueous layer was extracted with ethyl acetate. Combined the organic layers and washed with aqueous sodium chloride solution. Distilled off solvent completely from the organic layer to get tert-butyl (R)-3-(hydroxymethyl)hexanoate.Yield: 16.2 g.

tert-butyl (R)-3-(hydroxymethyl)hexanoate(1928755-17-2)Related Product Information

• Dihydro-4-propyl-2(3H)-furanone
• Brivaracetam (Racemate)
• Brivaracetam
• (R)-2-(2-(tert-butoxy)-2-oxoethyl)pentanoic acid
• (4S)-BrivaracetaM
• Brivaracetam (alfaR, 4R)-Isomer
• Brivaracetam (alfaR, 4S)-Isomer
• (Z)-2-propylhept-2-enal
• (R)-4-Propyldihydrofuran-2(3H)-one
• Brivaracetam Impurity 21
• Brivaracetam Impurity 9
• (R)-N-((S)-1-amino-1-oxobutan-2-yl)-3-(bromomethyl)hexanamide
• Brivaracetam Impurity 5
• (R)-Ethyl 3-(bromomethyl)hexanoate
• Brivaracetam Impurity 10
• Brivaracetam Impurity B
• Brivaracetam Impurity 11
• Brivaracetam Impurity 14