Reacción #49069

Ecuación de reacción

sodium borohydride

1-(1-pyrrolidinyl)cyclopentane carbonitrile

phenyllithium

D2

Racemic {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine

→

title compound

Rendimiento 56.0%

(±)1-Phenyl-1-[1-(1-pyrrolidinyl)cyclopentyl]methanamine

Rendimiento 56.0%

Disolventes

THF

methanol

dibutylether

Condiciones de reacción

Procedimiento

The title compound (0.55 g, 56%) was prepared from 1-(1-pyrrolidinyl)cyclopentane carbonitrile D9 (0.66 g, 4 mmol), and phenyllithium in dibutylether (2.4 ml of a 1.8M solution; 4.4 mmol) in THF (4 ml), followed by reaction with sodium borohydride (0.456 g, 12 mmol) in methanol (4 ml) in a similar manner to that described in D2. 1H NMR (CDCl3) δ: 0.41 (1H, m), 1.17 (1H, m), 1.35 (2H, m), 1.60 (2H, m), 1.73 (5H, m), 1.84-2.02 (3H, m), 2.64-2.74 (4H, m), 4.27 (1H, s), 7.21-7.31 (3H, m), 7.48 (2H, m).

Fuente