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

Temperature

-18 °C

Into a 300 ml flask, 30 ml of acetonitrile was introduced. It was then cooled to -18° C. At this temperature, a solution in which 10.0 g (75.8 mmol) of cis-(-)-1,2-epoxyindan (VI: optical purity: 94.0% e.e.) had been dissolved in 10 ml of acetonitrile as well as 11.5 g (113.6 mmol) of 97% sulfuric acid were dropwise added thereto independently at the same time in a period of 2 hours 30 minutes. Then, the reaction liquid was returned to room temperature. When 72 ml of water was added to the reaction liquid, a white crystal deposited. The reaction mixture was heated while being stirred. Under normal pressure, 75 ml of a water/acetonitrile azeotrope was distilled off. The remaining mixture was stirred for 1 hour under a reflux. The white crystal of the oxazoline derivative disappeared to form a transparent solution. This reaction liquid was cooled to room temperature and washed twice with 50 ml of dichloromethane. The pH of the water phase was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide. The grayish white scaly crystal deposited thereby was filtered off under reduced pressure, washed with a small quantity of water, and then dried in vacuo to yield 6.78 g (yield: 60.0%) of cis-(+)-1- aminoindan-2-ol (V). The chemical purity and optical purity of this crystal were 98.2% and 98.2% e.e., respectively.

1. additionwere dropwise added
2. customThen, the reaction liquid
3. customwas returned to room temperature
4. temperatureThe reaction mixture was heated
5. distillationUnder normal pressure, 75 ml of a water/acetonitrile azeotrope was distilled off
6. stirringThe remaining mixture was stirred for 1 hour under a reflux
7. customto form a transparent solution
8. customThis reaction liquid
9. temperaturewas cooled to room temperature
10. washwashed twice with 50 ml of dichloromethane
11. additionThe pH of the water phase was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide
12. filtrationThe grayish white scaly crystal deposited thereby was filtered off under reduced pressure
13. washwashed with a small quantity of water
14. customdried in vacuo

ORD record

ord-6cb5ddd9a07b4282b60b4bd3225fca18

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05648534