1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10374617, compound

4-Pentynoic acid (500 mg, 5.1 mmol), EDCI (1.56 g, 7.7 mmol) and HOBt (1.411 g, 10.2 mmol) were dissolved in 20 mL of DCM under inert atmosphere. A mixture of pyrrolidine (850 uL, 10.2 mmol) and DIPEA (4.5 mL, 25.5 mmol) in 3 mL DCM was added and the mixture was stirred for 2 h. The mixture was quenched with 25 mL 10% citric acid, stirred for 5 min., the organic layer was collected and the aqueous layer was extracted with 2×20 mL DCM. The combined organic layers were washed with 20 mL 10% citric acid. The DCM layer was washed with 20 mL saturated sodium bicarbonate, 20 mL brine and dried over sodium sulfate. The filtrates were concentrated and the residue was adsorbed on silica gel and chromatographed on silica gel (12 g) using 0→20% EtOAc-DCM to give 620 mg of 1-(pyrrolidin-1-yl)pent-4-yn-1-one.

1. additionwas added
2. customThe mixture was quenched with 25 mL 10% citric acid
3. stirringstirred for 5 min.
4. customthe organic layer was collected
5. extractionthe aqueous layer was extracted with 2×20 mL DCM
6. washThe combined organic layers were washed with 20 mL 10% citric acid
7. washThe DCM layer was washed with 20 mL saturated sodium bicarbonate, 20 mL brine
8. dry with materialdried over sodium sulfate
9. concentrationThe filtrates were concentrated
10. customchromatographed on silica gel (12 g)

ORD record

ord-533147cc913d411fa5fdf3e2d93a7480

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785470B2