Acetic Anhydride → HCID 86682892, compound

Temperature

85 °C

A suspension of 2,2-dimethylsuccinic acid (10.5 g, 71.7 mmol) in acetic anhydride (50 mL) was heated at 85° C. for 30 minutes and then concentrated under reduced pressure. The residue was dissolved in toluene (150 mL) and (S)-2-aminopropan-1-ol (6.0 g, 80 mmol) was added. The mixture was heated at reflux for 1 h under nitrogen atmosphere and cooled to room temperature. The solvent was removed under reduced pressure, and the residue was heated in acetic anhydride (50 mL) at 80° C. under nitrogen overnight. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was purified on a silica gel column (eluting with PE/EA=3/1) to afford (S)-2-(3,3-dimethyl-2,5-dioxopyrrolidin-1-yl)propyl acetate (10.1 g, 62.3%). 1H-NMR (CDCl3) δ 4.41 (m, 2H), 4.25 (m, 1H), 2.50 (s, 2H), 1.97 (s, 3H), 0.137 (d, 3H), 1.29 (s, 3H), 1.28 (s, 3H).

1. concentrationconcentrated under reduced pressure
2. dissolutionThe residue was dissolved in toluene (150 mL)
3. temperatureThe mixture was heated
4. temperatureat reflux for 1 h under nitrogen atmosphere
5. temperaturecooled to room temperature
6. customThe solvent was removed under reduced pressure
7. temperaturethe residue was heated in acetic anhydride (50 mL) at 80° C. under nitrogen overnight
8. temperatureThe reaction mixture was cooled to room temperature
9. customthe solvent was removed under reduced pressure
10. customThe residue was purified on a silica gel column (eluting with PE/EA=3/1)

ORD record

ord-316dc4eca9c542fb8cad73d869bd0906

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703810B2