Dimethylamine → (3-Bromo-phenyl)-dimethylamino-acetic acid ethyl ester

HRID 886602Notes

Reaction equation

HRID 886602 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)=O)[CH3:2].[CH3:15][NH:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)[N:16]([CH3:17])[CH3:15])[CH3:2]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 12252915ethyl 2-(3-bromophenyl)-2-oxoacetate

Product 1

HCID 59825088(3-Bromo-phenyl)-dimethylamino-acetic acid ethyl esterYield 16%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of (3-bromo-phenyl)-oxo-acetic acid ethyl ester (2.0 g, 7.8 mmol), dimethylamine (19.5 mL, 2 N in THF, 39 mmol), and sodium triacetoxyborohydride (4.95 g, 23.4 mmol) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 36 hours. Satuated sodium bicarbonate (50 mL) was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane to afford (3-bromo-phenyl)-dimethylamino-acetic acid ethyl ester (350 mg, 16%) as an oil. MS: m/z 286 (M+H+).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-abcc9b7693224808adff274f53e91c51
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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