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

HRID 976956

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

Reactant 5

HCID 962Water

HCID 1118Sulfuric Acid

HCID 6342Acetonitrile

HCID 14798Sodium Hydroxide

HCID 20758cis-1,2-Indandiol

Product 1

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

Conditions

Temperature: 0 °C

Procedure

Cis-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.

Workup

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

Sources & evidence

ORD record: ord-e75ea48617e8497492e1911921de0bc3
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05612484

Linked notes

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