Reaction #1274

Reaction equation

acetonitrile

Methanesulfonic acid

Indene oxide

Water

→

cis 1-amino-2-indanol

Solvents

methylene chloride

Conditions

Workup

1. 1
   TemperatureThe mixture was warmed to 25° C. and aged for 2 h
2. 2
   Temperaturethe mixture heated at 45° C. for 5 h
3. 3
   OtherThe organic phase was separated
4. 4
   Temperaturethe aqueous phase further heated
5. 5
   Temperatureat reflux for 4 h with concentration to approximately 200 g/L
6. 6
   Temperaturecooled to 5° C.
7. 7
   Filtrationfiltered
8. 8
   Otherdried in vacuo

Procedure

Indene oxide (117 g) diluted to a total volume of 600 mL in methylene chloride was diluted with acetonitrile (600 mL) and cooled to -20° C. Methanesulfonic acid (114 mL) was then added. The mixture was warmed to 25° C. and aged for 2 h. Water (600 mL) was added and the mixture heated at 45° C. for 5 h. The organic phase was separated and the aqueous phase further heated at reflux for 4 h with concentration to approximately 200 g/L. The solution was adjusted to pH 12.5 with 50% aqueous sodium hydroxide, and then cooled to 5° C. and filtered, dried in vacuo, to provide cis 1-amino-2-indanol.

Source