2-Amino-2-methyl-1,3-propanediol → Nsc57599

A flask with 2-amino-2-methyl-1,3-propanediol (3.32 g, 31.6 mmol) and diethyl carbonate (10 ml, 83 mmol) was fitted with a Dean-Stark trap and condenser and the suspension heated to 140° C. until 5 ml of liquid had been collected in the trap (˜8 hr). The solution was cooled to RT slowly, and the resulting white, block crystals were filtered off (2.79 g, 21.3 mmol, 67%). The supernatant was purified by flash chromatography to afford the title compound as a white solid (1.04 g, 7.94 mmol, 25%). 1H NMR (CDCl3, 400 MHz) δ 1.36 (s, 3H), 2.2 (br s, 1H), 3.56 (m, 2H), 4.06 (d, J=8.8 Hz, 1H), 4.33 (d, J=8.8 Hz, 1H), 5.2-5.3 (br s, 1H). ESI/APCI calculated for C5H9NO3: 131.06. Found: 132 (MH+).

1. customhad been collected in the trap (˜8 hr)
2. filtrationthe resulting white, block crystals were filtered off (2.79 g, 21.3 mmol, 67%)
3. customThe supernatant was purified by flash chromatography

ORD record

ord-1deb8a4d597b4bc185f7feb9c332b345

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722715B2