Acetic Acid → (1R,2S)-(+)-cis-1-Amino-2-indanol

Participants

Reaction Conditions

Reaction Steps

Into a 200 ml four-neck flask, 50 ml of acetic acid, 21.3 g (0.1 mol) of trans-(±)-2-bromoindan-1-ol (I), and 4.52 g (0.11 mol) of acetonitrile were introduced. While the mixture was stirred, 12.1 g (0.12 mol) of 97% sulfuric acid was dropwise added thereto at 23°-25° C. in a period of 35 minutes. The crystal totally disappeared. The reaction liquid was further stirred at room temperature for 20 hours. When dispersed into 200 ml of water, the reaction liquid became a white slurry. As this slurry was heated at 60° C. for 6 hours while being stirred, the crystal was totally dissolved. The reaction liquid was cooled to room temperature, washed twice with 100 ml of methylene chloride, and then subjected to liquid separation. When an aqueous solution of 25% sodium hydroxide was added to the water phase to attain a pH of 11, a white crystal was deposited. This crystal was filtered off under reduced pressure, washed with 100 ml of water, and then dried in vacuo to yield 5.33 g of cis-(±)-1-aminoindan-2-ol (I) as a white crystal. Its purity determined by a liquid chromatography was 96.9%.

Provenance & Evidence