반응 #1802508

반응 방정식

Water

H2O

Boron tribromide

4-[1-(4-methoxy-benzyl)-4,4-dimethyl-2-oxo-pyrrolidin-3-yloxy]-2-trifluoromethyl-benzonitrile

product

4-[1-(4-Methoxy-benzyl)-4,4-dimethyl-2-oxo-pyrrolidin-3-yloxy]-2-trifluoromethyl-benzonitrile

→

4-[1-(4-Hydroxy-benzyl)-4,4-dimethyl-2-oxo-pyrrolidin-3-yloxy]-2-trifluoromethyl-benzonitrile

용매

dichloromethane

반응 조건

후처리

1. 1
   추출the product was extracted into dichloromethane
2. 2
   세척The organic layer was washed with water and brine
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타The crude material was purified by flash column chromatography
7. 7
   기타(Procedure of example 8 will be referred to as a “demthylation reaction hereinafter”) MS (APCl, M+1) 405.0 LCMS

실험 절차

Boron tribromide (3 eq.) was added dropwise to a −78° C. solution of 4-[1-(4-methoxy-benzyl)-4,4-dimethyl-2-oxo-pyrrolidin-3-yloxy]-2-trifluoromethyl-benzonitrile (220 mg, 1_eq. in dichloromethane, i.e. the product of example 7). The reaction was allowed to gradually warm to ambient temperature overnight. Water was carefully added to the reaction and the product was extracted into dichloromethane. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate, filtered and concentrated. The crude material was purified by flash column chromatography. (Procedure of example 8 will be referred to as a “demthylation reaction hereinafter”) MS (APCl, M+1) 405.0 LCMS: 50-2% H2O, 214 nm, 2.390 min, 100%

출처