Ethanol → (+/-) cis-1-Phenoxy-2-methylaminoindane Hydrochloride

HRID 965241Notes

Reaction equation

HRID 965241 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]([C@@H:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C@@H:15]1[NH:23][C:24](OC(C)(C)C)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O1CCCC1.C(O)C.C(Cl)(Cl)[Cl:40]>>[ClH:40].[O:7]([C@@H:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C@@H:15]1[NH:23][CH3:24])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 6212ChloroformHCID 8028TetrahydrofuranHCID 18661301(+/-)cis-1-Phenoxy-2-tert-butoxycarbonylaminoindaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 70069143(+/-) cis-1-Phenoxy-2-methylaminoindane Hydrochloride

Procedure

The title compound was prepared in a similar manner to Example 12 from LiAlH4 (250 mg, 6.5 mmol), (±) cis-1-phenoxy-2-tert-butoxycarbonylaminoindane (425 mg, 1.3 mmol) and tetrahydrofuran (30 ml). After a reaction time of 2 h the reaction was worked up as previously described and subjected to column chromatography on silica gel eluting with 5% ethanol in chloroform to afford a colourless oil (290 mg) which was converted to the HCl salt and crystallised to afford the title compound as a white solid. m.p. >215° C. dec. (from methanol-diethyl ether).

Workup

  1. customAfter a reaction time of 2 h

Sources & evidence

ORD record
ord-0c7ea2b3aa034e4c86c0108ac27c8e4d
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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