Benzoyl chloride → N-benzyl-N-[(1S)-1-phenylprop-2-en-1-yl]cyclopentanamine

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Reaction Steps

To a solution of N-[(1S)-1-phenylprop-2-en-1-yl]cyclopentanamine (24 mg) and diisopropylamine (18 mg) in DCM (2.5 ml) at RT under N2 was added benzoyl chloride (20 mg). This mixture was stirred for 1 h. The reaction was evaporated and purified by flash chromatography (2% EtOAc/hexane) to afford the title compound (15 mg, 44%) as a pale oil. 1H NMR (300 MHz, CDCl3) δ 1.22-2.27 (m, 8H), 3.57 (bs, 1H), 5.28-5.60 (m, 3H), 6.23 (bs, 1H), 7.00-7.71 (m, 10H). MS APCI, m/z=306 (M+1), LC/MS, 2.83 min. Chiral HPLC was used to determine ee % by comparing this sample to a known sample of the racemic compound N-benzyl-N-(1-phenylprop-2-en-1-yl)cyclopentanamine. 14.99 min (97.89%) and 17.52 min (2.11%) or 96% ee. Chiral HPLC method: Chiral Technologies 10 μm Chiralpak AD column 4.6 mm×250 mm. Solvents: A=IPA, B=Hexane. Isocratic Method 7% A/B over 30 minutes at 0.6 ml/mn.

Provenance & Evidence