Ethanamine, 2,2,2-trifluoro- → HCID 59787429, compound

HRID 1965967Notes

Reaction equation

HRID 1965967 reaction equation
Cl.[CH:2]([C:4]1[CH:5]=[C:6]([B:10]([OH:12])[OH:11])[CH:7]=[CH:8][CH:9]=1)=O.[F:13][C:14]([F:18])([F:17])[CH2:15][NH2:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:13][C:14]([F:18])([F:17])[CH2:15][NH:16][CH2:2][C:4]1[CH:5]=[C:6]([B:10]([OH:12])[OH:11])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 5049666Sodium triacetoxyborohydrideHCID 86622779HCID 86622779, compound

Product 1

HCID 59787429HCID 59787429, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-formylphenyl boronic acid hydrochloride (2.5 g, 16.67 mmol) and 2,2,2,-trifluoroethylamine (2.97 g, 30.01 mmol) in DCM (100 mL). Add sodium triacetoxyborohydride (10.6 g, 50.02 mmol) portionwise over 10 min and stir the resulting solution for 72 h. Then quench with water (50 mw). Dry the organic fraction over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with dichloromethane:methanol (1:0 to 19:1) to give the title compound as a colourless oil (1.41 g, 36%).

Workup

  1. customThen quench with water (50 mw)
  2. dry with materialDry the organic fraction over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with dichloromethane:methanol (1:0 to 19:1)

Sources & evidence

ORD record
ord-2d6793eb4e724be5aa2267315b07e167
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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