Trimethylamine → HCID 46897088, compound

HRID 1928671Notes

Reaction equation

HRID 1928671 reaction equation
[CH3:1][C:2]1[O:8][CH:7]=[C:6]([OH:9])[C:4](=[O:5])[CH:3]=1.CN(C)C.[C:14](OC(=O)C)(=[O:16])[CH3:15]>C1COCC1>[C:14]([O:9][C:6]1[C:4](=[O:5])[CH:3]=[C:2]([CH3:1])[O:8][CH:7]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 7918Acetic AnhydrideHCID 695214H-Pyran-4-one, 5-hydroxy-2-methyl-

Product 1

HCID 46897088HCID 46897088, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Allomaltol (600 mg; 4.76 mmol) was weighed out into a round bottom flask (100 ml) containing a stir-bar. The contents were diluted with anhydrous THF (˜20 ml) and stirred (˜5 min) to afford a solution. Next, trimethyl amine (833 μl; 6.33 mmol; 1.33 equiv.) was added drop-wise and the contents stirred (˜5 min). Acetic anhydride (641 μl; 5.00 mmol) was then added drop-wise, capped and stirred at room temperature. The reaction was monitored via silica gel TLC. Once complete, the reaction mixture was concentrated under reduced pressure and the contents purified by silica gel chromatography to afford 650 mg product (3.87 mmol; 81% yield). This compound was found to have an EC50 of 106 μM. 1H NMR (DMSO-d6) δ 8.39 (s, 1H; 2-H); 6.36 (s, 1H; 5-H); 2.30 (s, 3H); 2.24 (s, 3H).

Workup

  1. addition(100 ml) containing a stir-bar
  2. customto afford a solution
  3. stirringthe contents stirred (˜5 min)
  4. customcapped
  5. stirringstirred at room temperature
  6. concentrationOnce complete, the reaction mixture was concentrated under reduced pressure
  7. customthe contents purified by silica gel chromatography

Sources & evidence

ORD record
ord-72ec73c0159e41dfa948089c4e7dc93a
Source dataset
uspto-grants-2012_05
Patent number
US08183398B2

Reaction notes

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