Allyl bromide → N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)ethylenediamine
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([C:12](=[O:17])[C:13]([F:15])([F:16])[F:14])[CH2:22][CH:21]=[CH2:20])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)ethylenediamine (562mg, 100%).
Workup
- stirringStir for 2.5 hours
- extractionextract with water (25 mL)
- customSeparate the organic phase
- washwash with brine (2×20 mL)
- extractionExtract the combined aqueous phases with ethyl acetate (2×5 mL)
- dry with materialdry (Na2SO4)
- customevaporate the solvent in vacuo
- customPurify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-033ad69494314f6f94e761ab776b92ee
- Source dataset
- uspto-grants-1996_02
- Patent number
- US05491142
Reaction notes
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