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

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Reaction Conditions

Reaction Steps

Into a 10 ml eggplant-type flask, 1.07 g (5.0 mmol) of trans-(+)-2-bromo-1-indanol (I: X=OH, Y=Br; optical purity: 81.6% e.e.) and 2.6 ml of acetonitrile were introduced. While this mixture was stirred with a magnetic stirrer and cooled in a water bath, 0.76 g (7.5 mmol) of 97% sulfuric acid was dropwise added thereto in a period of 2 hours. The resulting mixture was stirred at room temperature for 1 hour and then 6.5 ml of water was added thereto. After an acetonitrile/water azeotrope was distilled off under a reduced pressure of 200 mmHg at a bath temperature of 40° C., the remaining mixture was heated to 80° C. under normal pressure and then stirred at the same temperature for 4.5 hours. This reaction liquid was cooled to room temperature and then washed twice with 10 ml of dichloromethane. After a liquid separation, the pH of the water phase was adjusted to 11 by an addition of an aqueous solution of 25% sodium hydroxide. This phase was extracted with 10 ml of dichloromethane three times and then dried with sodium sulfate anhydride. After the solvent was distilled off from the remaining liquid, 0.60 g of a crude product was obtained. This product was dissolved in 97% sulfuric acid and then washed twice with 10 ml of dichloromethane. Thereafter, while this solution was cooled to room temperature, 25% sodium hydroxide was added thereto to attain a pH of 7. Then, the solution was washed twice with 10 ml of dichloromethane. By an addition of 25% sodium hydroxide, the pH of the solution was adjusted to 11. Thereafter, this solution was extracted with dichloromethane, dried with sodium sulfate anhydride, and then evaporated to dryness in vacuo to yield 0.38 g of cis-(-)-1-aminoindan-2-ol (V) as a white crystal (yield: 51.0%). According to an HPLC, its chemical purity and optical purity were 98.5% and 82.0% e.e., respectively.

Provenance & Evidence