BOC-(RS)-3-AMINO-1,2-PROPANEDIOL

616-30-8

24424-99-5

137618-48-5

GENERAL STEPS: 3-Amino-1,2-propanediol (3 g, 32.93 mmol, 1.0 eq.) was dissolved in a mixture of 20 mL of tert-butanol and 20 mL of 1 M NaOH. A 20 mL solution of tert-butanol containing di-tert-butyl dicarbonate (7.19 g, 32.93 mmol, 1.0 eq.) was slowly added under ice bath cooling conditions. The reaction mixture was stirred at room temperature for 5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete consumption of the raw materials, the reaction solution was concentrated under reduced pressure in a 50 °C water bath. Subsequently, the reaction mixture was neutralized with 1 M HCl solution. The neutralized solution was subjected to liquid-liquid extraction with ethyl acetate and water, which was repeated three times. The organic layers were combined, washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The dried organic phase was concentrated under reduced pressure in a water bath at 40 °C to give 6.3 g of tert-butyl N-(2,3-dihydroxypropyl)carbamate (yield: quantitative). The structure of the product was confirmed by 1H-NMR: 1H-NMR (500 MHz, CDCl3) δ 1.45 (9H, s), 2.68-2.71 (1H, br), 2.75-2.81 (1H, br), 3.20 (2H, dd), 3.63 (2H, dd), 3.71 (1H, m), 4.91 (1H, br).