Benzylethanolamine → Tert-butyl 2-(benzyl (2-hydroxyethyl)amino)acetate

To a solution of Compound 2 (1.86 g, 12.3 mmol) and potassium carbonate (1.70 g, 12.3 mmol) in CH3CN anhydrous (50 mL) at 0° C. was dropwise added t-Butyl-bromoacetate (2.41 g, 12.4 mmol) over 45 minute. The reaction mixture was gradually warmed to room temperature and stirred for 66 h. The resulting reaction mixture was filtered, and the filtrate was concentrated to give a white oily compound. The residue was then dissolved in CH2Cl2 (50 mL), and the resulting solution was filtered, and the filtrate was concentrated to afford white Compound 4 (2.94 g, 90%), 1H NMR (CDCl3) δ 1.45 (s, 9H), 2.86 (t, 2H), 3.23 (s, 2H), 3.54 to 3.62 (m, 2H), 3.82 (s, 2H), 7.23 to 7.34 (m, 5H); 13C NMR (CDCl3) δ 28.00, 55.27, 26.52, 58.47, 58.84, 81.29, 127.28, 128.36, 128.81, 138.27, 171.02. HRMS (Positive ion FAB) Calcd for C15H24NO3 [M+H]+ m/z 266.3605. Found: [M+H]+ m/z 266.1756.

1. customat 0° C.
2. customover 45 minute
3. customThe resulting reaction mixture
4. filtrationwas filtered
5. concentrationthe filtrate was concentrated
6. customto give a white oily compound
7. filtrationthe resulting solution was filtered
8. concentrationthe filtrate was concentrated

ORD record

ord-38fd95a8004e4fb997a5f6812feef8dc

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115094B2