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

In 40 ml of acetonitrile, 3.0 g (20.1 mmol) of trans-(-)-1,2-indandiol (I': trans-configuration: 98.0%; cis-configuration: 2.0%; optical purity: 100% e.e.) was dissolved. At room temperature, 3.2 g (31.7 mol) of 97% sulfuric acid was dropwise added thereto in a period of 30 minutes. After the resulting mixture was stirred at room temperature for 1 hour, the compound (I') disappeared from an HPLC. To the reaction liquid, 20 ml of water was added. Immediately thereafter, the mixture was heated and 42 ml of an acetonitrile/water azeotrope was distilled off under normal pressure. Then, the mixture was subjected to a reflux for 1.5 hours to complete the reaction. The reaction liquid was cooled to room temperature and washed twice with 10 ml of dichloromethane. Then, its pH 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 under reduced pressure to yield 1.77 g of cis-(-)-1-aminoindan-2-ol (V) as a primary crystal. Then, the mother liquid after the deposition of the crystal was extracted with dichloromethane and the extracted phase was concentrated to yield 0.69 g of the compound (V) as a secondary crystal.

1. dissolutionoptical purity: 100% e.e.) was dissolved
2. additionwas added
3. temperatureImmediately thereafter, the mixture was heated
4. distillation42 ml of an acetonitrile/water azeotrope was distilled off under normal pressure
5. temperaturea reflux for 1.5 hours
6. customthe reaction
7. customThe reaction liquid
8. temperaturewas cooled to room temperature
9. washwashed twice with 10 ml of dichloromethane
10. additionThen, its pH was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide
11. filtrationThe grayish white scaly crystal deposited thereby was filtered off under reduced pressure
12. washwashed with a small quantity of water
13. customdried under reduced pressure

ORD 기록

ord-27a0d904f04349609c60349b60ab7ad3

출처 데이터셋

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05760242