3-Amino-1-propanol → Benzyl N-(3-hydroxypropyl)carbamate

Temperature

0 °C

To a solution of 3-amino-1-propanol (3.75 g, 50 mmol) in methylene chloride (40 mL) was slowly added benzyl chloroformate (3.40 g, 20 mmol) in methylene chloride (10 mL) at 0° C. and the mixture was stirred at 0° C. for 3 h. Additional methylene chloride (50 mL) was added, the solution washed with 10% citric acid (3×50 mL) and brine (50 mL), and dried over Na2SO4. After evaporating the solvent in vacuo, the residue was purified by filtration through silica gel (1:1 ethyl acetate:hexane) to give the title compound as a white solid (4.05 g, 97%). 1H-NMR (300 MHz, CDCl3) δ 7.34 (m, 5H), 5.17 (bs, 11H), 5.10 (s, 2H), 3.66 (t, 2H, J=5.8 Hz), 3.33 (t, 2H, J=6.1 Hz), 2.63 (bs, 1H), 1.69 (pentet, 2H, J=6.1 Hz).

1. customat 0° C.
2. washthe solution washed with 10% citric acid (3×50 mL) and brine (50 mL)
3. dry with materialdried over Na2SO4
4. customAfter evaporating the solvent in vacuo
5. filtrationthe residue was purified by filtration through silica gel (1:1 ethyl acetate:hexane)

ORD record

ord-0cf080d0d1bd49199684303e2b928a60

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06417161B1