Bromoacetyl bromide → HCID 86666541, compound

Participants

Reaction Steps

4-((Allyloxycarbonyl)amino)butan-1-amine (87c, 1.18 g, 6.852 mmol, prepared according to Synthesis, 2002, 15, 2195) and proton sponge (1.468 g, 6.850 mmol) were dissolved in 14 mL of dichloromethane followed by the dropwise addition of 0.6 mL (6.908 mmol) of bromoacetyl bromide. After overnight stirring at room temperature, the mixture was diluted with dichloromethane, washed with water (2×) and brine (1×) and dried over sodium sulfate. The concentrated crude material was subjected to a Biotage™ flash chromatography system on a silica gel column with 40:1 (v/v) dichloromethane/methanol as the eluent. Product 88c (1.52 g, 76% yield) was obtained as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 1.69 (m, 4H), 3.22 (q, J=6.2, 2H), 3.32 (q, J=6.2, 2H), 3.88 (s, 2H), 4.56 (d, J=5.1, 2H), 4.80 (broad s, 1H), 5.21 (dd, J=1.1, 10.6, 1H), 5.30 (dd, J=1.8, 17.2, 1H), 5.92 (octet, J=5.6 Hz, 1H), 6.58 (broad s, 1H).

Provenance & Evidence