Triethylamine → HCID 89452617, compound

Trifluoroacetic anhydride (178 gm, 0.845 mol) was added slowly to a stirred solution of (2S)-tert-butyl 2-carbamoyl-5-oxopyrrolidine-1-carboxylate (IV) (97 gm, 0.425 mol), containing triethylamine (TEA) (193 gm, 1.907 mol) in dichloromethane (DCM) (2900 ml) at 0° C. After 2 hours of stirring, reaction mixture was diluted with water (1450 ml) and stirred further for 10 minutes. The organic layer was separated and washed with aqueous saturated solution of sodium hydrogen carbonate solution (500 ml), followed by brine (500 ml). The organic layer was dried over anhydrous sodium sulphate, and the solvent evaporated under reduced pressure. To the residue was added diethyl ether (200 ml), stirred well and the separated solid was filtered under suction to obtain the product. The filtrate was concentrated under reduced pressure and the residue was chromatographed on a column of silica gel using mixtures of ethyl acetate and hexane. The evaporation of the combined fractions gave 64.5 gm of (S)-tert-butyl 2-cyano-5-oxopyrrolidine-1-carboxylate (V) as white solid in 72% yield.

1. customreaction mixture
2. stirringstirred further for 10 minutes
3. customThe organic layer was separated
4. washwashed with aqueous saturated solution of sodium hydrogen carbonate solution (500 ml)
5. dry with materialThe organic layer was dried over anhydrous sodium sulphate
6. customthe solvent evaporated under reduced pressure
7. additionTo the residue was added diethyl ether (200 ml)
8. stirringstirred well
9. filtrationthe separated solid was filtered under suction
10. customto obtain the product
11. concentrationThe filtrate was concentrated under reduced pressure
12. customthe residue was chromatographed on a column of silica gel using mixtures of ethyl acetate and hexane
13. customThe evaporation of the combined fractions

ORD record

ord-d3497b5690e64cddb834fae7d9c3c35a

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115131B2