Butyl vinyl ether → HCID 59822296, compound

Participants

Reaction Steps

Combine 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.6 g, 1.41 mmol), butyl vinyl ether (0.9 mL, 7.06 mmol), palladium(II) acetate (32 mg, 0.14 mmol), DPPP (58 mg, 0.14 mmol), triethylamine (90.4 mL, 2.82 mmol), anhydrous DMF (10 mL) and stir at 90° C. for 2 h. Cool the reaction mixture to room temperature, add diethyl ether (25 mL) and wash with brine (15 mL). Separate the organic layer, dry over anhydrous Na2SO4, filter and concentrate in vacuo. Dissolve the residue in methanol (20 mL), add 1N aqueous HCl (18 mL) and stir at 70° C. for 2 h. Cool the reaction mixture to room temperature and remove methanol by evaporation. Dissolve the residue in diethyl ether (20 mL), wash with brine, collect the organic layer and dry over Na2SO4. Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 3:2 gradient) to obtain the desired intermediate as a colorless oil (0.4 g, 90%). MS (ES+) m/z: 320 (M+H)+.

Provenance & Evidence