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

HRID 1721017Notes

Reaction equation

HRID 1721017 reaction equation
[C@@H:1]1(O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[OH:10].S(=O)(=O)(O)O.O.[OH-].[Na+].C(#[N:22])C>>[NH2:22][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 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 6342Acetonitrile2×HCID 14798Sodium HydroxideHCID 247603trans-1,2-Indandiol

Product 1

HCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolYield 63%

Conditions

Temperature
0 °C

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).

Workup

  1. temperatureThe mixture was gradually warmed to 20° C. and aged to 3 hours
  2. temperaturethe mixture heated to reflux
  3. customThe resulting solid was removed by filtration

Sources & evidence

ORD record
ord-fd2f6e4902c44474af7c5366a6d0963b
Source dataset
uspto-grants-1996_04
Patent number
US05508404

Reaction notes

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