Phenyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate → 3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea
Reaction equation
[CH3:1][C:2]1([CH3:25])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=O)[O:17]C3C=CC=CC=3)=[CH:11][CH:10]=2)[O:3]1.[CH3:26][NH2:27].C1COCC1>C1COCC1>[CH3:26][NH:27][C:16]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:25])([CH3:1])[C:6]([CH3:8])([CH3:7])[O:5]2)=[CH:10][CH:11]=1)=[O:17]Participants
4
Procedure
A mixture of phenyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (26 g, 76.6 mmol)), 2.0M Methylamine/THF (265 mL, 530 mmol) in 150 mL of THF was stirred at room temperature for 6 hours, then excess solvent was distilled off from the reaction mixture; residue was dissolved into water, extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure. The crude product was purified by silica gel column chromatography by using 5-60% ethyl acetate in pet-ether as an eluent. to give 1-methyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-urea. (20 g, 88% yield) as white solid.
Workup
- distillationexcess solvent was distilled off from the reaction mixture
- dissolutionresidue was dissolved into water
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-21037de6cc13468a83db279e4ef05504
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575159B2
Reaction notes
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