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

HRID 965211Notes

Reaction equation

HRID 965211 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([S: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:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)C>[C:7]1([S: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:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54176936(+/-) trans 1-(Phenylthio)-2-ethoxycarbonylaminoindane

Product 1

HCID 54524531(+/-) trans 1-(Phenylthio)-2-methylaminoindaneYield 91.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of LiAlH4 (0.22 g, 5.7 mmol) in dry diethyl ether (10 ml) under nitrogen was added a solution of (±) trans 1-(phenylthio)-2-ethoxycarbonylaminoindane (0.36 g, 1.15 mmol) in diethyl ether (15 ml). After stirring overnight at room temperature the reaction was worked up as described in Preparation 4 to give the title compound as a brown oil (0.27 g) which was used in the next stage without purification.

Workup

  1. customas described in Preparation 4

Sources & evidence

ORD record
ord-1d9837dd4ad346ea8c936c6d1a4e7a15
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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