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

Beteiligte Stoffe

Reaktionsschritte

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 based on specific rotation: 42.5%) and 2.6 ml of acetonitrile were introduced. While this mixture was stirred with a magnetic stirrer, 0.76 g (7.5 mmol) of 97% sulfuric acid was dropwise added thereto in a period of 2 hours at room temperature. 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 40° C., the remaining mixture was stirred for 4.5 hours at 60° C. This reaction liquid was cooled to room temperature and then washed twice with 10 ml of dichloromethane. An aqueous solution of 25% sodium hydroxide was added to the water phase to attain a pH of 7. The resulting solution was washed twice with 10 ml of dichloromethane. Then, 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. The extracted phase was dried with sodium sulfate anhydride and then evaporated to dryness in vacuo to yield 0.47 g of cis-(+)-1-aminoindan-2-ol (V) as a white crystal (yield: 63.0%). According to an HPLC, its chemical purity and optical purity based on specific rotation were 98.8% and 42.0%, respectively.

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