Aluminium lithium hydride → (+/-) trans 1-(4-Benzylanilino)-2-methylaminoindane

HRID 965233Notes

Reaction equation

HRID 965233 reaction equation
[C:1]([C:9]1[CH:30]=[CH:29][C:12]([NH:13][C@@H:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][C@H:15]2[NH:23][C:24](OCC)=O)=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH2:1]([C:9]1[CH:30]=[CH:29][C:12]([NH:13][C@@H:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][C@H:15]2[NH:23][CH3:24])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54399733(+/-) trans 1-(4-Benzoylanilino)-2-ethoxycarbonylaminoindane

Product 1

HCID 54184078(+/-) trans 1-(4-Benzylanilino)-2-methylaminoindaneYield 70.6%

Procedure

(±) trans 1-(4-Benzoylanilino)-2-ethoxycarbonylaminoindane (1.0 g, 2.50 mmol) was reduced with LiAlH4 (0.95 g, 25.0 mmol) as described for Example 2. After stirring at room temperature for 2 days, the reaction was worked up as described for Example 2. Purification on a silica gel column using 0-2% ethanol in chloroform as eluant afforded a solid (0.58 g) which was recrystallised to give the title compound as a colourless solid, m.p. 137°-138° C. (from methanol/diethyl ether/n-pentane).

Workup

  1. customPurification on a silica gel column

Sources & evidence

ORD record
ord-2fbaadc2b8aa4c849b15cbf10c7b0efa
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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