Ethyl bromoacetate → HCID 54021629, compound

Temperature

-78 °C

Preparation of 3-Cyclobutyl-3-cyano-propionic acid ethyl ester—Cyclobutylacetonitrile (3.0 g, 3.5 mmol) is added to a solution of freshly prepared LDA (31.5 mmol) in 50 mL of THF at −78° C. After being stirred at −78° C. for 5 minutes, the anion solution is added over 10 minutes by cannula to a solution of ethylbromoacetate in 100 mL of THF at −78° C. The solution is stirred for 2 hours, then quenched with 20 mL of 1.0N HCl and warmed to room temperature. The THF is evaporated. The organics are extracted into CH2CL2 (3×50 mL), and the extracts are dried over Na2SO4. The solvent is evaporated, and the remaining oil is chromatographed by MPLC in 10% EtOAc/Hexanes to give 0.5 g (9% yield) of 3-cyclobutyl-3-cyano-propionic acid ethyl ester as an oil. NMR (1H, 400 MHz, CDCl3)δ1.3 (3H, t); 1.8-2.2 (6H, m); 2.5 (2H, dd); 2.5 (1H, m); 3.0 (1H, m); 4.2(2H, q).

1. stirringThe solution is stirred for 2 hours
2. customquenched with 20 mL of 1.0N HCl
3. temperaturewarmed to room temperature
4. customThe THF is evaporated
5. extractionThe organics are extracted into CH2CL2 (3×50 mL)
6. dry with materialthe extracts are dried over Na2SO4
7. customThe solvent is evaporated
8. customthe remaining oil is chromatographed by MPLC in 10% EtOAc/Hexanes

ORD record

ord-c8823eb3479c4cc591d49259d96c6d43

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627771B1