Reaction #1275

ord-0d0c32a5746a47be8dab7284d54a01f0

Reaction equation

[Na+].[OH-]
sodium hydroxide
O=S(=O)(O)O
sulfuric acid
O[C@@H]1Cc2ccccc2[C@H]1O
Trans-1,2-indandiol
CC#N
acetonitrile
CC#N
acetonitrile
O
Water
→
N[C@@H]1c2ccccc2C[C@@H]1O
cis-1-amino-2-indanol
Yield 63.0%

Reactants

[Na+].[OH-]
sodium hydroxide
O=S(=O)(O)O
sulfuric acid
O[C@@H]1Cc2ccccc2[C@H]1O
Trans-1,2-indandiol
CC#N
acetonitrile
CC#N
acetonitrile
O
Water

Reagents

None

Conditions

Temperature
0°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe mixture was gradually warmed to 20° C. and aged to 3 hours
  2. 2
    Temperaturethe mixture heated to reflux
  3. 3
    OtherThe resulting solid was removed by filtration

Procedure

Trans-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 (1.02 g, 63% yield).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723615uspto-grants-1998_03