Trifluoroacetic acid → HCID 67151741, compound

Temperature

80 °C

To a solution of (S,E)-tert-butyl 4-(4-bromostyryl)-2,2-dimethyloxazolidine-3-carboxylate (13 g) in acetonitrile (30 ml) were added sequentially water (35 ml) and a solution of trifluoroacetic acid (18.3 ml) in water (50 ml). The mixture was heated at 80° C. for 3 hours. The mixture was then cooled to room temperature and diluted with ethyl acetate/THF (1:1). The resulting mixture was washed sequentially with 1 N aq. sodium hydroxide solution and saturated brine, the phases were then separated and the organic phase was dried over sodium sulphate and concentrated in vacuo. The residue was triturated in diethyl ether (40 ml) and the resulting crystals were collected by filtration to afford (E)-(S)-2-amino-4-(4-bromo-phenyl)-but-3-en-1-ol (5.59 g, 68%) as a brown solid. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (SiO2; gradient: 0-30% MeOH in dichloromethane) to afford a further amount of (E)-(S)-2-amino-4-(4-bromo-phenyl)-but-3-en-1-ol (2.21 g, 27%) as a brown solid. MS (ISP): 227.1 ([{81Br}M+H—NH3]+), 225.1 ([{79Br}M+H—NH3]+).

1. temperatureThe mixture was then cooled to room temperature
2. washThe resulting mixture was washed sequentially with 1 N aq. sodium hydroxide solution and saturated brine
3. customthe phases were then separated
4. dry with materialthe organic phase was dried over sodium sulphate
5. concentrationconcentrated in vacuo
6. customThe residue was triturated in diethyl ether (40 ml)
7. filtrationthe resulting crystals were collected by filtration

ORD record

ord-24e974ecaa584fe08dc1172f26583443

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673950B2