Reaktion #49075

Reaktionsgleichung

sodium borohydride

2-(3-azabicyclo[3.1.0]hex-3-yl)-2-methylpropanenitrile

phenyllithium

D2

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

→

title compound

Ausbeute 44.0%

(±)2-(3-Azabicyclo[3.1.0]hex-3-yl)-2-methyl-1-phenyl-1-propanamine

Ausbeute 44.0%

Lösungsmittel

THF

methanol

dibutylether

Reaktionsbedingungen

Vorschrift

The title compound (393 mg, 44%) was prepared from 2-(3-azabicyclo[3.1.0]hex-3-yl)-2-methylpropanenitrile D15 (583 mg, 3.9 mmol), and phenyllithium in dibutylether (2.15 ml of a 2.0M solution; 4.3 mmol) in THF (7 ml), followed by reaction with sodium borohydride (445 mg, 11.7 mmol) in methanol (10 ml) in a similar manner to that described in D2. 1H NMR (CDCl3) δ: 0.38 (1H, m), 0.66 (1H, m), 0.74 (3H, s), 0.93 (3H, s), 1.30-1.40 (2H, m), 1.74 (2H, bs), 2.67 (2H, m), 2.91 (2H, t, J=8 Hz), 4.03 (1H, s), 7.20-7.30 (3H, m), 7.38 (2H, m).

Quelle