3-Amino-1-propanol → HCID 66773976, compound

HRID 1644814

Reaction equation

HRID 1644814 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4](Br)[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:20][CH2:21][CH2:22][CH2:23][OH:24]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)[NH:20][CH2:21][CH2:22][CH2:23][OH:24]

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 12717580Methyl 2-bromo-2-(4-fluorophenyl)acetate

Product 1

HCID 66773976HCID 66773976, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of bromo-(4-fluoro-phenyl)-acetic acid methyl ester (16.0 g) in chloroform (100 mL) was added potassium carbonate (17.9 g, finely ground) followed by 3-amino-1-propanol (4.87 g). The reaction was heated to 45° C. for 18 hours. The reaction was filtered and the filtrate was diluted with water and the phases were separated. The aqueous phase was further extracted with chloroform (3×25 mL) and the combined organics were washed with brine. The chloroform phase was dried over sodium sulfate, filtered and evaporated in vacuo to give the desired (4-fluoro-phenyl)-(3-hydroxy-propylamino)-acetic acid methyl ester (14.85 g, MS (ES+): 242.2 (MH+)) as a yellow oil which was used in the next step without further purification.

Workup

  1. filtrationThe reaction was filtered
  2. additionthe filtrate was diluted with water
  3. customthe phases were separated
  4. extractionThe aqueous phase was further extracted with chloroform (3×25 mL)
  5. washthe combined organics were washed with brine
  6. dry with materialThe chloroform phase was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-40afdde3d9d34abb9f55f3d86697f01a
Source dataset
uspto-grants-2012_02
Patent number
US08124636B2

Linked notes

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