Dimethylamine → HCID 46785681, compound
Reaction equation
[CH:1]([C:3]1[O:7][C:6]([B:8]([OH:10])[OH:9])=[CH:5][CH:4]=1)=O.[CH3:11][NH:12][CH3:13]>COCCOC.C1COCC1>[CH3:11][N:12]([CH2:1][C:3]1[O:7][C:6]([B:8]([OH:10])[OH:9])=[CH:5][CH:4]=1)[CH3:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (5-formyl-2-furyl)boronic acid (50 mg, 0.36 mmol) in DME (1.0 mL) was added a 2.0M solution of dimethylamine in THF (0.53 mL, 1.0 mmol). The reaction mixture stirred for 5 minutes before resin bound MP-BH(OAc)3 (2.2 mmol/g, 0.33 g, 0.714 mmol) was added. The reaction mixture was stirred at room temperature for five hours and an additional 1 equivalent of dimethylamine in THF was added and stirring continued overnight. The reaction mixture was filtered through a plug of glass wool and the resin was washed with DME. The THF/DME filtrate solution containing the desired compound was used immediately in subsequent reactions.
Workup
- additionwas added
- stirringThe reaction mixture was stirred at room temperature for five hours
- stirringstirring continued overnight
- filtrationThe reaction mixture was filtered through a plug of glass wool
- washthe resin was washed with DME
- additionThe THF/DME filtrate solution containing the desired compound
Sources & evidence
- ORD record
- ord-1228679c92374d369ec2c407e8849a56
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842803B2
Reaction notes
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