Dimethylamine → HCID 46785681, compound

HRID 1176181Notes

Reaction equation

HRID 1176181 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

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

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature for five hours
  3. stirringstirring continued overnight
  4. filtrationThe reaction mixture was filtered through a plug of glass wool
  5. washthe resin was washed with DME
  6. 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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