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

HRID 363820

Reaktionsgleichung

Reaktionsgleichung von HRID 363820
[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]

Komponenten

6

Edukt 5

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

Produkt 1

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

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-50f1d518bf34469ab84f752bf7f0c7e3
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874629

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