Hydrochloric Acid → (+/-)cis-1-(2-Benzylphenoxy)-2-methylaminoindane Hydrochloride
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:14]1[CH:37]=[CH:36][CH:35]=[CH:34][C:15]=1[O:16][C@@H:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C@@H:18]1[NH:26][C:27](OC(C)(C)C)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[ClH:38]>O1CCCC1>[ClH:38].[CH2:7]([C:14]1[CH:37]=[CH:36][CH:35]=[CH:34][C:15]=1[O:16][C@@H:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C@@H:18]1[NH:26][CH3:27])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Participants
5
Procedure
To a solution of LiAlH4 (436 mg, 12 mmol) in dry tetrahydrofuran (30 ml) under nitrogen was added dropwise a solution of (±)cis-1-(2-benzylphenoxy)-2-tert-butoxycarbonylaminoindane (500 mg, 1.2 mmol) in dry tetrahydrofuran (10 ml). The reaction was heated at reflux for 2 h then cooled with an ice/water bath and quenched with the minimum of water. The reaction was filtered and dried over Na2 SO4. Solvents were removed in vacuo and the residue subjected to column chromatography on silica gel eluting with 5% ethanol in chloroform to afford a colourless oil (356 mg,) which was converted to the HCl salt and crystallised to afford the title compound as a white solid. m.p. 191°-193° C. (from acetonediethyl ether).
Workup
- temperatureThe reaction was heated
- temperatureat reflux for 2 h
- temperaturethen cooled with an ice/water bath
- customquenched with the minimum of water
- filtrationThe reaction was filtered
- customdried over Na2 SO4
- customSolvents were removed in vacuo
- customto afford a colourless oil (356 mg,) which
- customcrystallised
Sources & evidence
- ORD record
- ord-2217565039bd450480ff24ac765cd006
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05773463
Reaction notes
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