Acetone → Methyl 2-(isopropylamino)acetate hydrochloride
Reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].[CH3:8][C:9]([CH3:11])=O.[OH-].[Na+]>CO.[Pd]>[ClH:1].[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][CH:9]([CH3:11])[CH3:8]Participants
6
Procedure
Part A: A mixture of glycine methyl ester hydrochloride (3.83 g, 30.5 mmol), acetone (1.77 g, 30.5 mmol) and NaOH (1.22 g, 30.5 mmol) in MeOH (200 mL) was stirred under an atmosphere of hydrogen (1 atm) in the presence of palladium on carbon (10%, 0.4 g) for 24 hours. The reaction was flushed with nitrogen and filtered through a Celite pad, acidified with HCl (1N), dried (MgSO4) and evaporated. Trituration of the residue with Et2O gave N-2-propylglycine methyl ester hydrochloride (1.0 g) as an off-white solid; LRMS (M+H)+ =132.1.
Workup
- customThe reaction was flushed with nitrogen
- filtrationfiltered through a Celite pad
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-99f47b7a6c2146e1925eb579793ac900
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06060462
Reaction notes
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