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

HRID 1451870Notes

Reaction equation

HRID 1451870 reaction equation
[CH2:1]([NH:8][C@H:9]([CH2:16]C)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)C1C=CC=CC=1.C([C@H](N)C1C=CC=CC=1)C>>[CH2:1]([NH:8][C@@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 6993773(1S)-1-phenylpropan-1-amineHCID 11368113HCID 11368113, compound

Product 1

HCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineYield 96%

Procedure

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.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e7aaefd3e7964ec3bf71fc7c094fae4f
Source dataset
uspto-grants-1997_02
Patent number
US05605914

Reaction notes

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