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

HRID 1180

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.C(#[N:20])C>>[NH2:20][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 4

HCID 962Water

HCID 1118Sulfuric Acid

HCID 6342Acetonitrile

HCID 20758cis-1,2-Indandiol

Product 1

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

Conditions

Temperature: -40 °C

Procedure

Cis-1,2-indandiol (1.0 g) was dissolved in acetonitrile (20 mL), cooled to -40° C., and fuming sulfuric acid (21% SO3, 0.8 mL) was added. The mixture was aged for 1 hour with gradual warming to 0° C. Water was added and the mixture heated to 80° C. for 1 hour to provide an aqueous solution of cis-1-amino-2-indanol.

Workup

temperaturewith gradual warming to 0° C
temperaturethe mixture heated to 80° C. for 1 hour

Sources & evidence

ORD record: ord-bb4572950e154c0d8d7ae87ec0fb230d
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723615

Linked notes

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