Lithium diisopropylamide → HCID 68666045, compound

Participants

Reaction Conditions

Reaction Steps

A solution of freshly prepared lithium diisopropylamide (0.75 mmol) in 5 mL of THF was added dropwise into a solution of trans N-tert-butyloxycarbonyl-5-(4-cyanophenyl)-3-(2-propenyl)-2-pyrrolidinone (223 mg, 0.68 mmol) in 5 mL of THF at −78° C. After stirring at −78° C. for 1 hr, the reaction was quenched by adding 5.0 mL of sat'd NH4Cl solution. The mixture was allowed to warm up to rt, and poured into a mixture of brine (20 mL) and CH2Cl2 (20 mL). The aqueous layer was separated and extracted with CH2Cl2 (3×20 mL). Organic layers were combined, dried over Na2SO4 and concentrated. Chromatography on a Biotage 40+S cartridge using 1:3 v/v EtOAc/hexanes as the eluant gave 103 mg (46%) of the title compound and 120 mg (54%) of starting material: 1H NMR δ 1.24 (s, 9H), 1.50-1.57 (m, 1H), 2.22-2.28 (m, 1H), 2.56-2.77 (m, 3H), 4.94-5.07 (m, 3H), 5.71-5.78 (m, 1H), 7.36 (d, J=8.2, 2H), 7.66 (d, J=8.2, 2H).

Provenance & Evidence