Water → (1R,2S)-(+)-cis-1-Amino-2-indanol
Reaction equation
[C@@H:1]1(O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[OH:10].S(=O)(=O)(O)O.O.[OH-].[Na+].C(#[N:22])C>>[NH2:22][C@@H:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[OH:10]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
Cis-1,2-indandiol (1.5 g) was dissolved in acetonitrile (25 mL) cooled to 0° C, and concentrated sulfuric acid (1.1 mL) was added. The mixture was gradually warmed to 20° C. and aged to 3 hours. Water (2 mL) was added and the mixture heated to reflux. Concentrated aqueous sodium hydroxide was added to adjust the pH to 12. The resulting solid was removed by filtration to provide an aqueous acetonitrile solution of cis-1-amino-2-indanol.
Workup
- temperatureThe mixture was gradually warmed to 20° C. and aged to 3 hours
- temperaturethe mixture heated to reflux
- customThe resulting solid was removed by filtration
Sources & evidence
- ORD record
- ord-e75ea48617e8497492e1911921de0bc3
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05612484
Reaction notes
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