Dimethylamine → HCID 58504275, compound

HRID 2407800Notes

Reaction equation

HRID 2407800 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:33][NH:34][CH3:35]>O1CCCC1>[CH3:33][N:34]([CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)[CH3:35]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 4321386Methyl 4-(3-formylphenyl)benzoateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58504275HCID 58504275, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3′-formylbiphenyl-4-carboxylate (0.338 g) was dissolved in 2 mol/L dimethylamine in tetrahydrofuran (20 mL) and stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.895 g) was added. The reaction was stirred at room temperature for 5 days and then partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organics were dried over magnesium sulfate and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 0-5% methanol/dichloromethane (0.5% triethylamine) to furnish the title compound (0.112 g) having the following physical data.

Workup

  1. stirringThe reaction was stirred at room temperature for 5 days
  2. custompartitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  3. dry with materialThe organics were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude material, which
  6. customwas purified by flash column chromatography (eluant

Sources & evidence

ORD record
ord-ba722ca47dfa4032884b0c26287b0228
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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