Dibenzylamine → HCID 66586829, compound

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Reaction Steps

The product was prepared by above general procedure and the same chemicals except employing dibenzylamine (1a′) (98 mg, 0.5 mmol), and methyl 5-oxopentanoate (2h′) (97 mg, 0.75 mmol). After 48 h, the crude product was purified by flash column chromatography (silica gel; ethyl acetate or diethyl ether/hexane=1:100) to afford the desired product 3h as a light yellowish oil (0.124g, 67% yield); Rf=0.54 (hexane:ethyl acetate=3:1); 1H NMR (CDCl3, 400 MHz) δ 7.33-7.27 (m, 8H), 7.25-7.19 (m, 2H), 4.44-4.42 (d, J=5.53 Hz, 1H), 3.82-3.63 (m, 4H), 3.55 (s, 3H), 3.363-3.359 (m, 6H), 2.78-2.73 (m, 1H), 2.53-2.26 (m, 2H), 1.86-1.70 (m, 2H) ppm; 13C NMR (CDCl3, 100 MHz) δ 174.2, 140.2 (C×2), 129.1 (CH×4), 128.1 (CH×4), 126.8 (CH2×2), 106.7, 56.6, 54.8, 54.2 (CH2×2), 53.6, 51.3, 31.1, 21.9 ppm; FTIR (neat): v=3017, 1454, 1215, 758, 494 cm−1; HRMS (ESI, m/z): calcd for C22H30NO4+ [M+H]+ 372.2175, found: 372.2178.

Provenance & Evidence