Benzaldehyde → (S)-(-)-N-Benzyl-1-phenylethylamine

Participants

Reaction Steps

Prepared as described earlier for N-benzyl-(R)-α-ethylbenzylamine from benzaldehyde (3.94 mL, 38.8 mmol) and (S)-α-ethylbenzylamine (5.0 mL, 38.8 mmol, 96% ee.) to afford 7.88 g (96%) of N-benzyl-(S)-α-methylbenzylamine as an oil contaminated with ~ 5% of benzyl alcohol and (S)-a-methylbenzylamine: 1H NMR (DMSO-d6, 250 MHz) δ 7.15-7.45 (m, 10 H, Ar), 3.69 (q, 1 H, J=6.5 Hz), 3.48 (dd, 2 H, J1 =13.6 Hz, J2 =20.9 Hz), 2.45 (br s, 1 H, NH), 1.26 (d, 3 H, J=6.5 Hz, CH3); 13C NMR (DMSO-d6) δ 146.0, 141.0, 128.1, 128.0, 127.8, 126.4, 126.3, 56.7, 50.6, 24.5. This mixture was directly used in the next reaction.

Provenance & Evidence