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

HRID 53297

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 6342Acetonitrile2×

HCID 14798Sodium Hydroxide

HCID 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

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-7a5d12c0d0194441817fba2295d984dc
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618937

Linked notes

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