Ethyl ketone → HCID 22346143, compound
Reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:16][CH2:17][C:18](=O)[CH2:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:17]([CH:18]([NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:19][CH3:20])[CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Benzyl 2-aminoethylcarbamate hydrochloride (2 g, 8.65 mmol) was dissolved in dichloromethane (50 ml) and 3-pentanone (3.7 ml, 35 mmol) was added. The reaction mixture was stirred for 1 hour at room temperature. Sodium triacetoxy borohydride (5.5 g, 26 mmol) was added and the reaction mixture was then stirred for 16 hours at room temperature. The solution was washed with saturated aqueous sodium hydrogen carbonate solution (40 ml). The dichloromethane phase was dried over anhydrous magnesium sulphate and the solvent was removed. The residues was purified by column chromatography on silica gel eluting with dichloromethane methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume). This gave the title compound as an oil (1.8 g).
Workup
- stirringthe reaction mixture was then stirred for 16 hours at room temperature
- washThe solution was washed with saturated aqueous sodium hydrogen carbonate solution (40 ml)
- dry with materialThe dichloromethane phase was dried over anhydrous magnesium sulphate
- customthe solvent was removed
- customThe residues was purified by column chromatography on silica gel eluting with dichloromethane methanol
Sources & evidence
- ORD record
- ord-f5c83767eb204fdc89261825f8de4fb0
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238676B2
Reaction notes
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