Hydrochloric Acid → HCID 55278056, compound

Participants

Reaction Steps

(R)-tert-Butyl(1-(3-chloro-2-fluorophenyl)allyl)carbamate: To a solution of crude Intermediate 6B (1.44 g, 4.97 mmol) in MeOH (10 mL) was added HCl (7 mL, 28.0 mmol) and stirred at rt for 1 h. Aliquot LCMS indicates that the starting material had been consumed. The reaction mixture was concentrated and coevaporated with toluene (2×). The crude product was then triturated with ether, filtered and then washed with ether to give (R)-1-(3-chloro-2-fluorophenyl)prop-2-en-1-amine as beige solid. The solid was dissolved in ACN (25 mL) and TEA (3.46 mL, 24.85 mmol) and to this solution was added Boc2O (1.50 mL, 6.46 mmol). The reaction was then stirred at rt overnight. The reaction mixture was diluted with EtOAc and washed with water followed by brine. The crude product was then purified using silica gel chromatography to give (R)-tert-butyl(1-(3-chloro-2-fluorophenyl)allyl)carbamate (835 mg, 59%) as a white solid. MS (ESI) m/z: 271.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.35-7.30 (m, 1H), 7.17 (td, J=7.0, 1.5 Hz, 1H), 7.09-7.03 (m, 1H), 6.03-5.92 (m, 1H), 5.48 (br. s., 1H), 5.26-5.11 (m, 2H), 1.49-1.35 (m, 9H) ppm.

Provenance & Evidence