73286-71-2,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.73286-71-2,N-Boc-2-pyrroline,as a common compound, the synthetic route is as follows.
Anhydrous toluene (150 ml), N-Boc 2-pyrroline (1.5 g; 8.9 mmol) and anhydrous lithium fluoride (23 mg; 0.88 mmol) were mixed under argon, and the mixture was heated to reflux. After 30 min TFDA (3.88 g; 15.5 mmol) in toluene solution (10 ml mixture volume) was added by 1 ml portions to the reaction mixture over 140 min, while reflux was continued. The reaction mixture was refluxed for additional 5 h. The solvent was removed under reduced pressure and resulting crude material was purified on a silica gel column using hexane-ethyl acetate 2:1 mixture as an eluent (Rf = 0.4). 1.01 g of the product was obtained as orange oil (yield 52%). 1H NMR (CDCl3, 500 MHz), Boc-rotamers (ratio 3:2): 3.86 and 3.71 (two br m, 1H, N-CH) 3.68 (br m, 1H, N-CHH), 3.28 and 3.15 (two br m, 1H, N-CHH), 2.19 (m, 3H, CH-CH2), 1.45 (s, 9H, CH3). 13C NMR (CDCl3, 126 MHz), Boc-rotamers: 154.3 (s, C=O), 111.9 (dd, J = 293 and 302 Hz, CF2), 80.0 (s, CMe3), 46.6 (br s, major) and 46.0 (br s, minor, N-CH2), 41.4 (dd, J = 11 and 15 Hz, N-CH), 27.9 (s, CH3), 26.7 (m, major) and 25.3 (m, minor, CH), 22.9 (s, minor) and 22.2 (s, major, CH2). 19F NMR (CDCl3, 376 MHz), Boc-rotamers: -128.9 (dd, JF-F = 161, JF-H = 11 Hz, major) and -129.3 (dm, JF-F = 160 Hz, minor, exo-F), -153.9 (d, JF-F = 160 Hz, minor) and -154.4 (d, JF-F = 161 Hz, major, endo-F). IR: 3076, 2974, 1683. Mass-spectrum (m/z): 200, 164 [M-tBu+1]. CHN (found/calc.): 54.40/54.79 C, 6.86/6.90 H, 6.42/6.39 N.
The synthetic route of 73286-71-2 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Kubyshkin, Vladimir; Kheylik, Yurii; Mykhailiuk, Pavel K.; Journal of Fluorine Chemistry; vol. 175; (2015); p. 73 – 83;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem