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

HRID 53298
Notes
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Reaction equation

HRID 53298 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 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

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

Sources & evidence

ORD record
ord-0067e158893844c9995a9aba06ba8064
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05618937

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes