Propane sultone → 3-[(1-Methoxypropan-2-yl)amino]propane-1-sulfonic acid

To a solution of 2-amino-1-methoxypropane (5.0 g, 17.8 mmol) in tetrahydrofuran (25 mL) was slowly added 1,3-propane sultone (2.12 g, 17.0 mmol). The mixture was stirred at reflux for 4 h. The reaction mixture was cooled to room temperature. The solid product was collected by filtration, washed with acetone (2×25 mL), and dried in a vacuum oven (50° C.), to afford compound EI (3.1 g, 86%). 1H NMR (D2O, 500 MHz) δ ppm 3.53 (m, 1H), 3.41 (m, 2H), 3.27 (s, 3H), 3.11 (m, 2H), 2.89 (t, 2H, J=7.3 Hz), 2.00 (m, 2H), 1.18 (d, 3H, J=5.9 Hz). 13C NMR (D2O, 125 MHz) δ ppm 71.73, 58.80, 53.79, 48.08, 43.55, 21.52, 12.79. ES-MS 210 (M−1).

1. temperatureat reflux for 4 h
2. filtrationThe solid product was collected by filtration
3. washwashed with acetone (2×25 mL)
4. customdried in a vacuum oven (50° C.)
5. customto afford compound EI (3.1 g, 86%)

ORD record

ord-49dbf2f2bd8a415d97135de77c0781c5

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642801B2