Réaction #1274

Équation de réaction

acetonitrile

Methanesulfonic acid

Indene oxide

Water

→

cis 1-amino-2-indanol

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was warmed to 25° C. and aged for 2 h
2. 2
   Températurethe mixture heated at 45° C. for 5 h
3. 3
   AutreThe organic phase was separated
4. 4
   Températurethe aqueous phase further heated
5. 5
   Températureat reflux for 4 h with concentration to approximately 200 g/L
6. 6
   Températurecooled to 5° C.
7. 7
   Filtrationfiltered
8. 8
   Autredried in vacuo

Mode opératoire

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