Phenethylamine → Diethylether hexane

To a stirred suspension of N-[(2-adamantyloxy)-carbonyl)-α-methyl-β-(2-pyridyl-1-oxide)-D,L-alanine (2.43 g, 6.5 mmol) in 150 mL dry tetrahydrofuran at -20° C. was added N-methylmorpholine (0.76 g, 7.5 mmol) and isobutyl chloroformate (1.02 g, 7.5 mmol). The mixture was stirred for 20 minutes at this temperature followed by addition of 2-phenethylamine (1.21 g, 10 mmol), stirred for 3 hours at -25° C., and then warmed to room temperature. The solvent was removed in vacuo at room temperature, and theresidue was diluted with ethyl acetate and water. The solution was washed with 5% citric acid (3×) and water (2×) followed by 5% potassium hydrogen carbonate (3×), water (2×), and brine. The organic phase was dried over magnesium sulfate. The solvent was removed invacuo to yield an oily residue which crystallized by addition of diethyl ether/n-hexane (2.76 g, 89% yield), m.p. 76°-80° C.

1. stirringstirred for 3 hours at -25° C.
2. customThe solvent was removed in vacuo at room temperature
3. additionwas diluted with ethyl acetate and water
4. washThe solution was washed with 5% citric acid (3×) and water (2×)
5. dry with materialThe organic phase was dried over magnesium sulfate
6. customThe solvent was removed invacuo
7. customto yield an oily residue which

ORD record

ord-4b49f840b49845ea942122fbbad64218

Source dataset

uspto-grants-1994_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05331006