Potassium Carbonate → {2-[2-(3-hydroxypropoxy)phenyl]ethyl}-N-methylcarbamic acid tert-butyl ester

Temperature

80 °C

N-(2-(2-Hydroxyphenyl)ethyl)-N-methylcarbamic acid tert-butyl ester (702 mg, 2.79 mmol) was dissolved in N,N-dimethylformamide (6 ml). Potassium carbonate (1.93 g, 13.97 mmol) and cesium chloride (24 mg, 0.14 mmol) were added. 3-bromo-1-propanol (0.28 ml, 3.07 mmol) was added. The reaction mixture was stirred at 80° C. for 16 h. It was cooled to room temperature and diluted with ethyl acetate (75 ml) and water (75 ml). The phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with a 10% aqueous solution of sodium hydrogen sulfate solution (70 ml) and a saturated aqueous solution of sodium hydrogen carbonate (70 ml). They were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (80 g), using ethyl acetate/heptane (1:1) as eluent, to give 606 mg of {2-[2-(3-hydroxypropoxy)phenyl]ethyl}-N-methylcarbamic acid tert-butyl ester.

1. temperatureIt was cooled to room temperature
2. customThe phases were separated
3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
4. washThe combined organic layers were washed with a 10% aqueous solution of sodium hydrogen sulfate solution (70 ml)
5. dry with materialThey were dried over magnesium sulfate
6. customThe solvent was removed in vacuo
7. customThe crude product was purified by flash chromatography on silica (80 g)

ORD record

ord-b1034021d1a2406aa060b9a7ab64b2f6

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127354