2-Bromobenzyl alcohol → HCID 68555942, compound

Temperature

-78 °C

A solution of (2-bromophenyl)methanol (56 g) in tetrahydrofuran (300 mL) was cooled to −78° C., n-butyllithium (1.6 M, hexane solution, 390 mL) was slowly added dropwise. After stirring at −78° C. for 1 hr, a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (60 g) in tetrahydrofuran (200 mL) was added dropwise. The reaction mixture was warmed to room temperature, and the mixture was stirred at room temperature overnight. The reaction was quenched with water and stirring at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, and washed with aqueous sodium chloride solution. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate, 40%-80%) and crystallized from ethyl acetate-hexane to give the object product (35 g).

1. temperatureThe reaction mixture was warmed to room temperature
2. stirringthe mixture was stirred at room temperature overnight
3. customThe reaction was quenched with water
4. stirringstirring at room temperature for 30 min
5. additionThe reaction mixture was diluted with ethyl acetate
6. washwashed with aqueous sodium chloride solution
7. dry with materialThe organic layer was dried over sodium sulfate
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate, 40%-80%)
10. customcrystallized from ethyl acetate-hexane

ORD record

ord-a3fb5596fd48413d8148e0e43b4fbfcd

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575167B2