Uses
N-(tert-Butoxycarbonyl)pyrrolidine-2-methanol is used to prepare 1,3-thiazolidin-2-imines derivatives as inhibitors of nitric oxide synthase.
Synthesis
Step 1. Synthesis of tert-butyl 2-hydroxymethylpyrrolidine-1-carboxylate
Pyrrolidine-2-methanol (0.300 g, 1.98 mmol) was dissolved in dichloromethane (5.0 mL) and di-tert-butyl dicarbonate (0.650 g, 1.98 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the residue was purified by post-processing using Isco Combi-Flash Companion column chromatography (eluent: dichloromethane solution in 0-10% methanol) to afford tert-butyl 2-hydroxymethylpyrrolidine-1-carboxylate (0.590 g, 98% yield).
1H NMR (CDCl3, 300 MHz) δ 4.78 (br d, 1H), 4.05-3.90 (br, 1H), 3.67-3.53 (m, 2H), 3.49-3.41 (m, 1H), 3.34-3.26 (m, 1H), 2.00 (dddd, 1H), 1.85-1.72 (m, 2H). 1.60-1.50 (m, 1H), 1.46 (s, 9H).
References
[1] Patent: US2017/253569, 2017, A1. Location in patent: Paragraph 0994-0995
[2] Tetrahedron, 2005, vol. 61, # 10, p. 2631 - 2643
[3] Patent: US2016/168090, 2016, A1. Location in patent: Paragraph 0823-0824
[4] Patent: WO2011/22508, 2011, A2. Location in patent: Page/Page column 59; 60
[5] Patent: EP2202223, 2010, A1. Location in patent: Page/Page column 72-73
