Reaction #1276

ord-bb4572950e154c0d8d7ae87ec0fb230d

Reaction equation

O[C@@H]1c2ccccc2C[C@@H]1O
Cis-1,2-indandiol
CC#N
acetonitrile
O=S(=O)(O)O
sulfuric acid
O
Water
→
N[C@@H]1c2ccccc2C[C@@H]1O
cis-1-amino-2-indanol

Reactants

O[C@@H]1c2ccccc2C[C@@H]1O
Cis-1,2-indandiol
CC#N
acetonitrile
O=S(=O)(O)O
sulfuric acid
O
Water

Reagents

None

Conditions

Temperature
-40°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewith gradual warming to 0° C
  2. 2
    Temperaturethe mixture heated to 80° C. for 1 hour

Procedure

Cis-1,2-indandiol (1.0 g) was dissolved in acetonitrile (20 mL), cooled to -40° C., and fuming sulfuric acid (21% SO3, 0.8 mL) was added. The mixture was aged for 1 hour with gradual warming to 0° C. Water was added and the mixture heated to 80° C. for 1 hour to provide an aqueous solution of cis-1-amino-2-indanol.

Source

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