(1S)-(+)-Camphor-10-sulphonic acid → 1H-Inden-2-amine, 5-bromo-2,3-dihydro-, (2R)-

HRID 1435717Notes

Reaction equation

HRID 1435717 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH2:11])[CH2:5]2.[C@:12]12([CH2:22][S:23]([OH:26])(=[O:25])=[O:24])[C:19]([CH3:21])([CH3:20])[CH:16]([CH2:17][CH2:18]1)[CH2:15][C:13]2=[O:14]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([NH2:11])[CH2:5]2.[C@:12]12([CH2:22][S:23]([OH:26])(=[O:24])=[O:25])[C:19]([CH3:21])([CH3:20])[CH:16]([CH2:17][CH2:18]1)[CH2:15][C:13]2=[O:14].[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([NH2:11])[CH2:5]2

Participants

4

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 112987955-bromo-2,3-dihydro-1H-inden-2-amine

Product 2

HCID 112758701H-Inden-2-amine, 5-bromo-2,3-dihydro-, (2R)-HCID 86588388(r)-5-bromo-2-aminoindan (1S)-(+)-10-camphorsulfonate salt

Procedure

The title compound was prepared using a similar method to that described in Prashad et al, Adv. Synth. Catal. 2001, 343, No. 5, pp 461-472: ie by resolution of the free base form of racemic 5-bromo-2-aminoindan using (1S)-(+)-10-camphorsulphonic acid to obtain (R)-5-bromo-2-aminoindan (1S)-(+)-10-camphorsulfonate salt. The enantiomeric purity of (R)-5-bromo-2-aminoindan (1S)-(+)-10-camphorsulfonate salt was checked by HPLC using the following conditions:

Sources & evidence

ORD record
ord-5acb0318df6347bf976386cbfec323ac
Source dataset
uspto-grants-2009_11
Patent number
US07618969B2

Reaction notes

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