Tetrahydrofuran → HCID 67156334, compound

Temperature

0 °C

(E)-(S)-2-amino-4-(4-bromo-phenyl)-but-3-en-1-ol (7.8 g) and N,N-diisopropylethylamine (11.1 ml) were combined with THF (150 ml) to give a colourless solution. The reaction mixture was cooled to 0° C. and di-tert-butyl carbonate (7.17 g) was added. The reaction mixture was stirred at room temperature overnight to afford a yellow solution. The reaction mixture was then poured into EtOAc and washed sequentially with 1 M aq. HCl, 1 M aq. NaOH and saturated brine. The organic layer was dried over Na2SO4, filtered, and the filtrate was then stirred over charcoal (2 g) for 30 min. The mixture was then filtered through celite and the filtrate was concentrated in vacuo to afford [(E)-(S)-3-(4-bromo-phenyl)-1-hydroxymethyl-allyl]-carbamic acid tert-butyl ester as an off-white solid (10.8 g, 98%). MS (ISP): 344.0 ([{81Br}M+H]+), 342.0 ([{79Br} M+H]+), 287.9 ([{81Br}M+H—C4H8]+), 286.0 ([{79Br} M+H—C4H8]+).

1. customto give a colourless solution
2. customto afford a yellow solution
3. washwashed sequentially with 1 M aq. HCl, 1 M aq. NaOH and saturated brine
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. stirringthe filtrate was then stirred over charcoal (2 g) for 30 min
7. filtrationThe mixture was then filtered through celite
8. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-dfbcc29aa849435399b2ee7cbfbeb382

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354441B2