Tert-butyl 3-hydroxy-2-(hydroxymethyl)-1-oxo-1-phenylpropan-2-ylcarbamate → 3-Hydroxy-2-(hydroxymethyl)-1-oxo-1-phenylpropan-2-aminium chloride

tert-butyl 3-hydroxy-2-(hydroxymethyl)-1-oxo-1-phenylpropan-2-ylcarbamate (1) (120 mg, 0.4 mmol, 1.0 equiv.) was added to a 10 mL RBF followed by a 4.0 N HCl-Dioxane solution (3.0 mL, 12.0 mmol, 30.0 equiv.). The solution was stirred for 1 h and 2 mL of the solvent was evaporated with a steady stream of N2 (g). The resulting suspension was taken up in Et2O giving a white precipitate. The mixture was filtered, washed with Et2O (3×10 mL) and dried under vacuum to give 77 mg (83%) of 3 as a white solid. Decomposition occurs at 173-174° C.; 1H NMR (500 MHz, DMSO) δ 8.51 (br s, 3H, C—NH3), 7.89 (d, J=7.5 Hz, 2H, Ph-H), 7.64 (t, J=7.5 Hz, 1H Ph-H), 7.53 (t, J=7.5 Hz, 2H, Ph-H), 5.77 (s, 2H, (CH2—OH)2), 4.11 (d, J=12.0 Hz, 2H, C—CH2), 3.89 (d, J=12.0 Hz, 2H, C—CH2); 13C NMR (125 MHz, DMSO) δ 197.6, 135.1, 132.7, 128.7, 128.1, 73.1, 61.2; LRMS (ESI-MS m/z): Mass calcd for C10H14NO3 [M]+, 296.22. Found 296. Anal. calcd for C10H14ClNO3: C, 51.84; H, 6.33; N, 6.05 Found: C, 51.70; H, 6.33; N, 5.84.

1. custom2 mL of the solvent was evaporated with a steady stream of N2 (g)
2. filtrationThe mixture was filtered
3. washwashed with Et2O (3×10 mL)
4. customdried under vacuum

ORD record

ord-852457e0537147009e571d8be535c422

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07329775B2