Ethanol → (+/-)cis-1-[(4-Phenoxy)phenoxy]-2-methylaminoindane Hydrochloride

HRID 965238Notes

Reaction equation

HRID 965238 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O: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].[O: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 21226445Aluminium lithium hydrideHCID 67646800(+/-)cis-1-[(4-Phenoxy)phenoxy]-2-tert-butoxycarbonylaminoindane

Product 1

HCID 70071152(+/-)cis-1-[(4-Phenoxy)phenoxy]-2-methylaminoindane Hydrochloride

Procedure

The title compound was prepared in a similar manner to Example 12 from LiAlH4 (760 mg, 20 mmol), (±)cis-1-[(4-phenoxy)phenoxy]-2-tert-butoxycarbonylaminoindane (1.39 mg, 3.3 mmol) and tetrahydrofuran (40 ml). After a reaction time of 3 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 pale pink oil (951 mg) which was converted to the HCl salt and crystallised to afford the title compound as a white solid. m.p. 188°-190° C. (from methanol-diethyl ether).

Workup

  1. customAfter a reaction time of 3 h

Sources & evidence

ORD record
ord-f5db633ee5144fab81bbe5a5caabac78
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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