Ethanol → (+/-)cis-1-(4-Benzylphenoxy)-2-methylaminoindane Hydrochloride

HRID 965240Notes

Reaction equation

HRID 965240 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:14]1[CH:37]=[CH:36][C:17]([O:18][C@@H:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][C@@H:20]2[NH:28][C:29](OC(C)(C)C)=O)=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O1CCCC1.C(O)C.C(Cl)(Cl)[Cl:47]>>[ClH:47].[CH2:7]([C:14]1[CH:37]=[CH:36][C:17]([O:18][C@@H:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][C@@H:20]2[NH:28][CH3:29])=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 6212ChloroformHCID 8028TetrahydrofuranHCID 18661294cis-1-(4-Benzylphenoxy)-2-tert-butoxycarbonylaminoindaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 18661293(+/-)cis-1-(4-Benzylphenoxy)-2-methylaminoindane Hydrochloride

Procedure

The title compound was prepared in a similar manner to Example 12 from LiAlH4 (320 mg, 8.4 mmol), cis-1-(4-benzylphenoxy)-2-tert-butoxycarbonylaminoindane (700 mg, 1.7 mmol) and tetrahydrofuran (40 ml). After a reaction time of 2.5 h the reaction was worked up as previously described and subjected to column chromatography on silica gel eluting with 2% ethanol in chloroform to afford a colourless oil (438 mg) which was converted to the HCl salt and crystallised to afford the title compound as a white solid. m.p. 222° C. dec. (from methanol-diethyl ether).

Workup

  1. customAfter a reaction time of 2.5 h

Sources & evidence

ORD record
ord-3f2de820fb754f6b8952cf3f0a61f8af
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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