Triethylamine → HCID 68685133, compound

HRID 2216656Notes

Reaction equation

HRID 2216656 reaction equation
[N:1]1[N:2]([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[N:3]=[CH:4][CH:5]=1.Cl.[CH3:15][O:16][C:17](=[O:20])[CH2:18][NH2:19].C(N(CC)CC)C.[O-]S([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.C1COCC1.CO>[CH3:15][O:16][C:17](=[O:20])[CH2:18][NH:19][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)=[CH:7][CH:8]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 122755Glycine methyl ester hydrochlorideHCID 4311764Sodium borohydrideHCID 107973024-(2H-1,2,3-triazol-2-yl)benzaldehyde

Product 1

HCID 68685133HCID 68685133, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 60 g (347 mmol) of 4-[1,2,3]-triazol-2-yl-benzaldehyde in 1000 ml of CH2Cl2, 78.9 g (629 mmol) of glycine methylester hydrochloride, 104.2 ml (749 mmol) of triethylamine and 150 g of MgSO4 are successively added at 0–5° C. The mixture is stirred at r.t. for 18 h and filtered through celite. The filtrate is concentrated under reduced pressure and the residue is diluted with AcOEt. Et3N hydrochloride is filtered off and the filtrate is concentrated under reduced pressure in an azeotropic manner using toluene to give the crude imine. To a solution of the crude imine in 600 ml of THF and 600 ml of MeOH, 20 g (526 mmol) of NaBH4 is added portionwise at −20˜−10° C. and the mixture is stirred for 1 h. The reaction mixture is slowly quenched with sat. aqueous NH4Cl and then extracted with CH2Cl2. The combined extracts are washed with H2O, brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by CC on silica gel (n-Hexane:AcOEt=2:1˜1:1) to provide the title compound.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. additionthe residue is diluted with AcOEt
  4. filtrationEt3N hydrochloride is filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure in an azeotropic manner
  6. customto give the crude imine
  7. stirringthe mixture is stirred for 1 h
  8. customThe reaction mixture is slowly quenched with sat. aqueous NH4Cl
  9. extractionextracted with CH2Cl2
  10. washThe combined extracts are washed with H2O, brine
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated under reduced pressure
  13. customThe residue is purified by CC on silica gel (n-Hexane:AcOEt=2:1˜1:1)

Sources & evidence

ORD record
ord-48060b873d454f509fe2a775f4bd065a
Source dataset
uspto-grants-2006_09
Patent number
US07112611B2

Reaction notes

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