Acetaldehyde → HCID 45092242, compound
Reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])([CH3:4])([CH3:3])[CH3:2].[CH:14](=O)[CH3:15].C([O-])([O-])=O.[K+].[K+].[BH4-].[Na+]>CO.O>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:14][CH3:15])([CH3:4])([CH3:2])[CH3:3]Participants
Conditions
- Temperature
- 0 °C
Procedure
A mixture of (4-amino-butyl)-carbamic acid tert-butyl ester (0.360 g, 1.91 mmol), acetaldehyde (0.085 g, 1.91 mmol) and K2CO3 (0.264 g, 1.91) in MeOH (5 mL) was stirred for 6 h. The mixture was filtered through a celite cake. The filtrate was cooled at 0° C. and NaBH4 (0.106 g, 2.08 mmol) was added. After the reaction mixture was stirred at 0° C. for 45 min water (20 mL) was added, and the mixture was extracted with CH2Cl2 (3×30 mL). The organic extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (200:10:1 CH2Cl2/MeOH/NH4OH), affording (4-ethylamino-butyl)-carbamic acid tert-butyl ester as a colorless oil (0.215 g, 52%).
Workup
- filtrationThe mixture was filtered through a celite cake
- additionwas added
- extractionthe mixture was extracted with CH2Cl2 (3×30 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationAfter filtration the solvent
- customwas removed by evaporation under vacuum
- customthe residue was purified by flash chromatography on a silica gel column (200:10:1 CH2Cl2/MeOH/NH4OH)
Sources & evidence
- ORD record
- ord-a13948580ee5418b8cff71a229682798
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863293B2
Reaction notes
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