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

HRID 1178

Reaction equation

HRID 1178 reaction equation
[CH:1]12[O:10][CH:2]1[CH2:3][C:4]1[C:9]2=[CH:8][CH:7]=[CH:6][CH:5]=1.CS(O)(=O)=O.O.C(#[N:19])C>C(Cl)Cl>[NH2:19][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

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 6395Methanesulfonic AcidHCID 92838Indene oxide

Product 1

HCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

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.

Workup

  1. temperatureThe mixture was warmed to 25° C. and aged for 2 h
  2. temperaturethe mixture heated at 45° C. for 5 h
  3. customThe organic phase was separated
  4. temperaturethe aqueous phase further heated
  5. temperatureat reflux for 4 h with concentration to approximately 200 g/L
  6. temperaturecooled to 5° C.
  7. filtrationfiltered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-5cabef20e3d4416cbf3328a8863028c7
Source dataset
uspto-grants-1998_03
Patent number
US05723615

Linked notes

Loading…