Propanal → methyl 9-bromo-1-propyl-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1.[CH:19](=O)[CH2:20][CH3:21].O>ClCCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:13]([CH2:19][CH2:20][CH3:21])[CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1Participants
5
Procedure
To a solution of methyl 9-bromo-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate (2.0 g) in 1,2-dichloroethane (20 ml) were added propion aldehyde (1.87 g) and triacetoxy sodium borohydride (4.11 g) and the mixture was stirred overnight. Water was added and the mixture was extracted with ethyl acetate, after which it was washed with aqueous saturated sodium bicarbonate solution and saturated brine, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give methyl 9-bromo-1-propyl-2,3,4,5-tetrahydro-1H-1-benzoazonin-6-carboxylate (2.15 g) as a yellow oily material.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washafter which it was washed with aqueous saturated sodium bicarbonate solution and saturated brine
- dry with materialdried with magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)
Sources & evidence
- ORD record
- ord-e0d32f39160849fb9dae077213ea4bb5
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183273B2
Reaction notes
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