(Diethylamino)sulfur trifluoride → rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-fluoro-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

温度

0 °C

A cooled (−78° C.) mixture of DAST (117 mg; 0.72 mmol) in anh. DCM (0.5 ml) was treated dropwise with a solution of rac-(3R*,5S*)-5-(2,6-dimethoxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)benzyl)-pyrrolidin-2-one (100 mg; 0.24 mmol) in anh. DCM (0.5 ml). The resulting mixture was further stirred at −78° C., under nitrogen, for 1 h, at 0° C. for 30 min., and finally at rt for 1 h. Aq. sat. NaHCO3 was added, and the resulting mixture was extracted with DCM. The mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by preparative HPLC afforded rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-fluoro-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one as a colorless solid. LC-MS (conditions A): tR=0.90 min.; [M+H]+: 414.12 g/mol.

1. temperatureA cooled
2. waitfinally at rt for 1 h
3. extractionthe resulting mixture was extracted with DCM
4. dry with materialThe mixed organic layers were dried over anh. MgSO4
5. filtrationfiltered
6. concentrationconcentrated to dryness under reduced pressure
7. customPurification by preparative HPLC

ORDレコード

ord-c0b9d84504a04bdc85d64d379bc519cb

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09242970B2