Diethyl Carbonate → HCID 11116891, compound

Temperature

135 °C

(1S,2S)-2-Amino-1-phenylpropane-1,3-diol (20.0 g, 120 mmol), diethyl carbonate (29.7 mL, 245 mmol), and K2CO3 (1.65 g, 12.0 mmol) were charged into a flask with mechanical stirrer and a vigreux-column. This suspension was heated in an oil bath at 135° C., to give a yellow solution. The accrued EtOH was distilled off over the vigreux column. The reaction was stirred over a period of 3 h, until no more EtOH could be distilled off. The reaction mixture was then cooled to 50° C., diluted with EtOAc and aqueous NaHCO3. The organic layers were separated, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (550 g SiO2) using EtOAc in heptane from 33% to 100% in order to give the title compound as a beige oil (7.50 g, 33%). 1H NMR (400 MHz, DMSO-d5): 7.87 (br s, 1H), 7.50-7.30 (m, 5H), 5.37 (d, 1H), 5.23-5.17 (m, 1H), 3.70-3.60 (m, 1H), 3.60-3.50 (m, 2H).

1. customto give a yellow solution
2. distillationThe accrued EtOH was distilled off over the vigreux column
3. distillationcould be distilled off
4. temperatureThe reaction mixture was then cooled to 50° C.
5. additiondiluted with EtOAc and aqueous NaHCO3
6. customThe organic layers were separated
7. washwashed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by column chromatography (550 g SiO2)

ORD record

ord-4b1fdcf100f94ff996843b5973f67745

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296733B2