Acetic Acid → 1-(4-Fluoro-phenyl)-2-[4(pyrazin-2-yloxy)-benzyl amino]-ethanol

HRID 1160206Notes

Reaction equation

HRID 1160206 reaction equation
C([BH3-])#N.[Na+].[NH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[OH:8].[N:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.C(O)(=O)C>CO>[F:15][C:12]1[CH:13]=[CH:14][C:9]([CH:7]([OH:8])[CH2:6][NH:5][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([O:22][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][N:16]=3)=[CH:24][CH:25]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 98272-Amino-1-(4-fluorophenyl)ethan-1-olHCID 36144114-(Pyrazin-2-yloxy)benzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 684330321-(4-Fluoro-phenyl)-2-[4(pyrazin-2-yloxy)-benzyl amino]-ethanolYield 35.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (0.62 mL, 1 M in THF) was added to a solution of 2-amino-1-(4-fluoro-phenyl)-ethanol (80 mg, 0.52 mmol), 4-(Pyrazin-2-yloxy)-benzaldehyde (103 mg, 0.52 mmol) and glacial acetic acid (0.5 mL), in methanol (3 mL) at RT and the flask was stirred overnight. The reaction mixture was concentrated in vacuo; the residue was quenched with saturated aqueous sodium bicarbonate solution and then extracted with dichloromethane (3×4 mL). The combined organic phases were dried over anhydrous sodium sulfate and concentrated again in vacuo to yield 1-(4-fluoro-phenyl)-2-[4(pyrazin-2-yloxy)-benzyl amino]-ethanol as a white solid 62 mg, 35%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was quenched with saturated aqueous sodium bicarbonate solution
  3. extractionextracted with dichloromethane (3×4 mL)
  4. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  5. concentrationconcentrated again in vacuo

Sources & evidence

ORD record
ord-5785338dbe8142e1ae257bab1d2179f2
Source dataset
uspto-grants-2010_10
Patent number
US07816354B2

Reaction notes

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