Hydrogen Peroxide → HCID 58380936, compound

Participants

Reaction Steps

1-(1-aminopropyl)-1-(4-fluorophenyl)cyclopent-3-ene (118, 348 mg, 1.6 mmol) was dissolved in THF at 0° C. under argon. Borane (1.75 mL, 1.75 mmol, 1M in THF) was added dropwise over 10 minutes. The reaction mixture was allowed to warm to room temperature before stirring overnight. After cooling to 0° C., water was added (4 mL), followed by hydrogen peroxide (0.61 mL, 30% solution in water) and sodium hydroxide solution (1.75 mL, 1M aqueous solution). After stirring for 5 minutes the mixture was extracted with ethyl acetate, dried over sodium sulphate and evaporated to give 458 mg of desired product, which was stirred for 15 minutes with dilute hydrochloric acid (10 mL, 2M aqueous solution). Evaporation, followed by freeze drying gave 514 mg of the desired product as mixture of four stereoisomers as a colourless hydrochloride salt. Rt=1.83, 1.99, 2.36, 2.86 min (Method 2). Detected mass: 203.1 (M—NH3—H2O+H+).

Provenance & Evidence