Reacción #49097

Ecuación de reacción

phenyllithium

sodium borohydride

(±)-1-(2-methyl-1-pyrrolidinyl)cyclopentanecarbonitrile

methanol

→

ammonia

title compound

Rendimiento 46.0%

(±)-[[1-(2-methyl-1-pyrrolidinyl)cyclopentyl](phenyl)methyl]amine

Rendimiento 46.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroReaction
2. 2
   Temperaturacooled to 0° C.
3. 3
   Otroto react at 20° C. overnight
4. 4
   TemperaturaThe reaction was cooled to 0° C.
5. 5
   Otroquenched with saturated sodium bicarbonate
6. 6
   Extracciónextracted with ethyl acetate
7. 7
   Secadodried (Na2SO4)
8. 8
   Otroevaporated
9. 9
   OtroThe product was purified by chromatography on a 5 g SCX column
10. 10
    Lavadoeluting from 0-100% ethyl acetate in pet. ether, 0-10% methanol in ethyl acetate

Procedimiento

A solution of (±)-1-(2-methyl-1-pyrrolidinyl)cyclopentanecarbonitrile D39 (0.997 g; 5.6 mmol) in dry THF was cooled to −70° C. To this phenyllithium (1.7M in C6H14/ether, 1.1 equiv) was added slowly. The whole mixture was allowed to warm slowly to room temperature over 3 h with stirring under argon. Reaction cooled to 0° C. and methanol added followed by sodium borohydride (portionwise) and allowed to react at 20° C. overnight. The reaction was cooled to 0° C. and quenched with saturated sodium bicarbonate, extracted with ethyl acetate, dried (Na2SO4) and evaporated. The product was purified by chromatography on a 5 g SCX column eluting from 0-100% ethyl acetate in pet. ether, 0-10% methanol in ethyl acetate then 2% 0.880 ammonia in ethyl acetate to give the title compound as an oil (0.67 g; 46%) was obtained. Mass Spectrum (Electrospray LC/MS): Found 259 (MH+). C17H26N2 requires 258. Ret. time 1.19 min.

Fuente