Tert-Butylamine → 1-tert-Butyl-3-hydroxyazetidine

Temperatur

25 °C

To a solution of tert-butylamine (10 mmol) in isopropylalcohol (20 mL) was added dropwise epichlorohydrine (10 mmol). The mixture was stirred at 25° C. for 16 h. After concentration, the residue was re-dissolved in acetonitrile (20 mL) and triethylamine (20 mmol) was added. The mixture was heated at 100° C. for 24 h, cooled to rt and filtered. The filtrate was concentrated providing 1-tert-butyl-azetidin-3-ol (1.1 g). MS (ESI): mass calcd. for C7H15NO, 129.1; m/z found, 130.1 [M+H]+. 1H NMR (CDCl3): 6.15-5.70 (br s, 1H), 4.84-4.72 (m, 1H), 4.24-4.12 (m, 2H), 4.03-3.87 (m, 2H), 1.37 (s, 9H).

1. concentrationAfter concentration
2. dissolutionthe residue was re-dissolved in acetonitrile (20 mL)
3. temperatureThe mixture was heated at 100° C. for 24 h
4. temperaturecooled to rt
5. filtrationfiltered
6. concentrationThe filtrate was concentrated

ORD-Eintrag

ord-dc15a146c38a427ba4879dbf23510fc1

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08642583B2