Ammonium Chloride → rac-(S*)-5-(2,6-dimethoxyphenyl)-3-methylene-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

温度

0 °C

A cooled (−78° C.) mixture of methyltriphenylphosphonium bromide (754 mg; 2.11 mmol) in anh. THF (6 ml) was treated dropwise with a solution of n-BuLi (1.6 M in hexanes; 1.32 ml; 2.11 mmol). Stirring was then continued at rt, under nitrogen, for 30 min. The resulting mixture was then cooled to 0° C., and treated with a solution of 5-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)-benzyl)pyrrolidine-2,3-dione (800 mg; 1.95 mmol) in anh. THF (4 ml). Stirring was continued at 0° C. for 25 min., and at 60° C. for 1 h. After cooling to rt, aq. sat. NH4Cl (25 ml) was added, and this mixture was extracted with AcOEt (3×50 ml). The mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=30/1) afforded rac-(S*)-5-(2,6-dimethoxyphenyl)-3-methylene-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one as a colorless oil. LC-MS (conditions A): tR=0.93 min.; [M+H]+: 408.29 g/mol.

1. temperatureA cooled
2. stirringStirring
3. waitwas continued at 0° C. for 25 min.
4. waitat 60° C. for 1 h
5. temperatureAfter cooling to rt
6. extractionthis mixture was extracted with AcOEt (3×50 ml)
7. dry with materialThe mixed organic layers were dried over anh. MgSO4
8. filtrationfiltered
9. concentrationconcentrated to dryness under reduced pressure
10. customPurification by FC (DCM/MeOH=30/1)

ORDレコード

ord-8b38badd18fb4bab95412ba068111d6f

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09242970B2