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

反応式

[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]

参加物

反応物 5

HCID 962Water

HCID 1118Sulfuric Acid

HCID 6342Acetonitrile2 回

HCID 14798Sodium Hydroxide

HCID 247603trans-1,2-Indandiol

生成物 1

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

反応条件

温度: 0 °C

実験手順

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).