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

Participants

Reaction Conditions

Reaction Steps

Into a 300 ml flask, 30 ml of acetonitrile was introduced. It was then cooled to -16° C. At this temperature, a solution in which 10.0 g (75.8 mmol) of cis-(+)-1,2-epoxyindan (VI: optical purity: 95.1% 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 10 minutes. The cooling was stopped so that the reaction liquid gradually returned to room temperature. When 72 ml of water was added thereto, a white crystal deposited. The reaction mixture was heated and 74 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 6.69 g (yield: 59.3%) of cis-(-)-1-aminoindan-2-ol (V). The chemical purity and optical purity of this crystal were 96.9% and 99.6% e.e., respectively.

Provenance & Evidence