6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]-ethoxy]hexanamide → 1-[2-[(6-aminohexyl)oxy]-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole
Reaction equation
[N:1]1([CH2:6][CH:7]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH2:16])=O)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:16][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH:7]([CH2:17][O:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1Participants
Procedure
6-[2-(1H-Imidazol-1-yl)-1[[4-methoxyphenyl)methoxy]methyl]ethoxy]hexanamide (Example 20, 0.3 g, 0.0008 mol) in dry tetrahydrofuran (2 ml) was added to a stirred suspension of lithium aluminium hydride (0.5 g, 0.013 mol) in dry tetrahydrofuran (10 ml) under a nitrogen atmosphere. The resulting suspension was stirred under reflux for 24 hours cooled to room temperature and the residual lithium aluminium hydride destroyed using ethyl acetate (15 ml) followed by dilute sodium hydroxide solution (2N, 20 ml), the resulting solution was filtered and the filter cake was washed with ethyl acetate (50 ml), the organic layer was separated, dried (MgSO4) and evaporated to an oil which was purified by column chromatography (silica gel, ethylacetate to 10% methanol in ethyl acetate) to yield the title compound as an oil.
Workup
- temperatureunder reflux for 24 hours
- customthe residual lithium aluminium hydride destroyed
- filtrationthe resulting solution was filtered
- washthe filter cake was washed with ethyl acetate (50 ml)
- customthe organic layer was separated
- dry with materialdried (MgSO4)
- customevaporated to an oil which
- customwas purified by column chromatography (silica gel, ethylacetate to 10% methanol in ethyl acetate)
Sources & evidence
- ORD record
- ord-fd87b5f3526b4cd7aa3e2e3df1a43693
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04758573
Reaction notes
Loading…