Ammonium Hydroxide → Methyl 4-amino-1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1)=[O:4].[BH4-].[Na+].[OH-].[NH4+:22]>>[CH3:1][O:2][C:3]([C:5]1[CH2:6][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:9][C:10]=1[NH2:22])=[O:4]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
rac-1-Benzyl-4-oxo-piperidine-3-carboxylic acid methyl ester (25 g) was suspended in 100 ml ammonium hydroxide 25% and heated at 50° C. during 18 h. The mixture was cooled with ice and then, NaBH4 (1 g) was added in several portions. Stirring was continued for 18 h at ambient temperature and the mixture was diluted with water/ice, with cooling, and extracted with AcOEt. The organic extract was washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a brown oil which was purified by column chromatography (silica gel, heptane/AcOEt, 1/1) and precipitated (AcOEt/heptane) to give 12.1 g (56%) of the title compound as white solid and 6 g (25%) of the title compound as its borane salt.
Workup
- temperatureThe mixture was cooled with ice
- temperaturewith cooling
- extractionextracted with AcOEt
- extractionThe organic extract
- washwas washed with brine
- dry with materialdried over sodium sulfate
- customRemoval of the solvent under reduced pressure
- customgave a brown oil which
- customwas purified by column chromatography (silica gel, heptane/AcOEt, 1/1)
- customprecipitated (AcOEt/heptane)
Sources & evidence
- ORD record
- ord-5877dabc6f8049898ff9e4b835bbc8ad
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683079B2
Reaction notes
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