HCID 21639277, compound → 3-Pyrrolidinepropanol

A solution of 3-(1H-pyrrol-3-yl)-1-propanol (400 mg, 3.20 mmol) in 5 mL of freshly distilled glacial acetic acid containing 40 mg of platinum(IV) oxide was hydrogenated with a H2 balloon for 2 h at 35° C. The catalyst was removed by filtration, and the solvent was evaporated. The residue was heated under reflux for 0.5 h with 4 mL of 30% aqueous NaOH solution to saponify any acetate ester that may have formed. The mixture was extracted with CH2Cl2, and the organic phase was concentrated to obtain the crude pyrrolidine (0.35 g, 85%) as a light-yellow oil, which could be used without purification in the following step. 1H NMR (CDCl3, 300 MHz) δ 3.66 (t, 2H, J=6.3 Hz), 2.62 (dd, 1H, J=7.2, 10.5 Hz), 2.91-2.99 (m, 2H), 2.51 (dd, 1H, J=7.2, 10.8 Hz), 1.93-2.15 (m, 2H), 1.56-1.65 (m, 2H), 1.46 (t, 2H, J=7.2 Hz), 1.37-1.41 (m, 2H). LC-MS (ESI) m/z 130 (M+H+).

1. customThe catalyst was removed by filtration
2. customthe solvent was evaporated
3. temperatureThe residue was heated
4. temperatureunder reflux for 0.5 h with 4 mL of 30% aqueous NaOH solution
5. custommay have formed
6. extractionThe mixture was extracted with CH2Cl2
7. concentrationthe organic phase was concentrated

ORD record

ord-5ede1e9b3d7443a8aef4c84955cbae28

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445684B2