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

Participants

Reaction Steps

Into a 200 ml four-neck flask, 9.24 g (70 mmol) of cis-(±)-1,2-epoxyindan (IV) and 35 ml of acetonitrile were introduced. While the mixture was stirred in cool, 10.62 g of 97% sulfuric acid was dropwise added thereto at 20°-25° C. in a period of 30 minutes. The reaction mixture was further stirred at room temperature for 1 hour. Then, acetonitrile was distilled off under reduced pressure. The remaining mixture was further stirred at 60° C. for 1 hour and then cooled to room temperature. Impurities were extracted off from the mixture with 20 ml and 10 ml of methylene chloride. An aqueous solution of 25% sodium hydroxide was added to the water phase to attain a pH of 11. The crystal deposited thereby was filtered off and then dried in vacuo to yield 4.76 g (raw yield: 45.7%) of cis-(±)-1-aminoindan-2-ol (V) as a grayish white crystal. From thus obtained crystal, 2 g was taken out and washed with 6 ml of acetonitrile at 10° C. The washed crystal was filtered off and then dried in vacuo to yield 1.68 g of the aimed product (V) as a white crystal. Its purity determined by a liquid chromatography was 98.9%.

Provenance & Evidence