Water → methyl 4-methoxyphenethylcarbamate

Temperature

0 °C

To a solution of 4-methoxy-phenethylamine (5.81 mL, 39.7 mmol) in anhydrous THF (200 mL) was added Et3N (6.6 mL, 48 mmol). The solution was cooled to 0° C. and methyl chloroformate (15.38 mL, 199 mmol) was added slowly via syringe. The reaction was stirred at 0° C. for 2 hours and then allowed to warm to room temperature and stirred overnight. To the reaction mixture was added H2O (50 mL) and the resulting solution was extracted into Et2O (1×100 mL) and then into EtOAc (2×75 mL). The combined organic fractions were washed with brine (200 mL) and 1 M HCl (200 mL), dried over Na2SO4, filtered and concentrated under vacuum, affording 7.98 g (96%) of the title compound as a pale yellow solid.

1. temperatureto warm to room temperature
2. stirringstirred overnight
3. extractionthe resulting solution was extracted into Et2O (1×100 mL)
4. washThe combined organic fractions were washed with brine (200 mL) and 1 M HCl (200 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under vacuum

ORD record

ord-57627c7987e04701ac6af90be2659b3f

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245780B1