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).
