1,4-Dioxane hydrochloride → 3-Hydroxy-1-oxo-1-phenylpropan-2-aminium chloride

tert-butyl 3-hydroxy-1-oxo-1-phenylpropan-2-ylcarbamate (19) (270 mg, 1.0 mmol, 1.0 equiv) was added to a 25 mL RBF and a 4.0 N HCl-Dioxane solution (7.5 mL, 30.0 mmol, 30.0 equiv.) was added. The solution was stirred at rt. for 25 min, and 5 mL dioxane was evaporated with a steady stream of N2 (g). Next, Et2O (10 mL) was added to the reaction flask and a white precipitate formed. The soln was stirred for 10 min and filtered with a Buchner funnel. The precipitate was dried under vacuum to give 170 mg (86%) of 6 as a white solid. mp=160-162° C.; 1H NMR (500 MHz, DMSO) δ 8.94 (s, 3H, CH—NH3) 8.07 (d, J=7.0 Hz, 2H, Ph-H), 7.73 (t, J=7.0 Hz, 1H, Ph-H), 7.59 (t, J=7.5 Hz, 2H, Ph-H), 5.53 (br s, 1H, CH2—OH), 5.19 (s, 1H, +NH3—CH), 3.94 (d, J=11.5 Hz, 1H, CH—CH2), 3.85 (d, J=11.5 Hz, 1H, CH—CH2); 13C NMR (125 MHz, DMSO) δ 194.5, 134.3, 133.7, 129.1, 128.8, 60.6, 57.6; LRMS (ESI-MS, n/z): Mass calcd for C9H12NO2 [M]+, 166.20. Found 166. Anal. calcd for C9H12ClNO2: C, 53.61; H, 6.00; N, 6.95 Found: C, 53.26; H, 6.13; N, 6.96.

1. custom5 mL dioxane was evaporated with a steady stream of N2 (g)
2. additionNext, Et2O (10 mL) was added to the reaction flask
3. customa white precipitate formed
4. stirringThe soln was stirred for 10 min
5. filtrationfiltered with a Buchner funnel
6. customThe precipitate was dried under vacuum

ORD record

ord-a733ecc26d7243f0abded7042db334f4

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07329775B2