Sodium borohydride → (+/-)1-[1-(1-Azetidinyl)cyclopentyl]-1-phenylmethanamine

Participants

Reaction Steps

The title compound (0.45 g, 47%) was prepared from 1-(1-azetidinyl)cyclopentanecarbonitrile D13 (0.60 g, 4.0 mmol), and phenyllithium in ethers (2.6 ml of a 1.7M solution; 4.4 mmol) in THF (5 ml), followed by reaction with sodium borohydride (0.456 g, 12 mmol) in methanol (5 ml) in a similar manner to that described in D2. 1H NMR (CDCl3) δ: 0.67 (1H, m), 1.06 (1H, m), 1.32 (4H, m), 1.48 (2H, m), 1.91-2.03 (4H, m), 3.24 (4H, m), 3.83 (1H, s), 7.20-7.32 (3H, m), 7.44 (2H, m).

Provenance & Evidence