Reacción #170906

Ecuación de reacción

Methyl 4-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-bromobenzoate

LiBH4

→

1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamide

Rendimiento 74.0%

Disolventes

THF ether H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction was quenched with H2O (10 mL)
2. 2
   workup.ADDITIONThe reaction mixture was diluted with dichloromethane (25 mL)
3. 3
   Extracciónwas extracted with 1N HCl (30 mL×3) and brine (30 mL)
4. 4
   SecadoThe organic extracts were dried over Na2SO4
5. 5
   Otroevaporated
6. 6
   OtroThe crude product was purified by chromatography on silica gel (eluting with 0-100% ethyl acetate in hexanes)

Procedimiento

Methyl 4-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-bromobenzoate (4.12 g, 9.9 mmol) was added to a solution of LiBH4 (429 mg, 19.8 mmol) in THF/ether/H2O (20/20/1 mL) and was allowed to stir at 25° C. After 16 hours, the reaction was quenched with H2O (10 mL). The reaction mixture was diluted with dichloromethane (25 mL) and was extracted with 1N HCl (30 mL×3) and brine (30 mL). The organic extracts were dried over Na2SO4 and evaporated. The crude product was purified by chromatography on silica gel (eluting with 0-100% ethyl acetate in hexanes) to afford 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamide (2.84 g, 74%). ESI-MS m/z calc. 389.0. found 390.1 (M+1)+; retention time 2.91 minutes.

Fuente