Benzylethanolamine → HCID 178499151, compound

HRID 2110185Notes

Reaction equation

HRID 2110185 reaction equation
[CH:1]([C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])=O.[O-]S([O-])(=O)=O.[Na+].[Na+].[CH2:19]([NH:26][CH2:27][CH2:28][OH:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:19]([N:26]([CH2:1][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])[CH2:27][CH2:28][OH:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 4348BenzylethanolamineHCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 178499152Methyl 5-formyl-1H-imidazole-4-carboxylate

Product 1

HCID 178499151HCID 178499151, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of Intermediate 1C (3.20 g, 20.76 mmol) in dry THF (180 mL) was added anhydrous Na2SO4 (14.48 g, 192 mmol) and N-benzylethanolamine (3.70 g, 24.47 mmol). The resulting mixture was stirred at room temperature under nitrogen for 1 hour. Sodium triacetoxyborohydride (6.37 g, 28.5 mmol) was added portion-wise and the resulting mixture was stirred under nitrogen for 48 hours. The resulting mixture was quenched with water and neutralized with saturated NaHCO3 solution. The mixture was extracted with DCM and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated. The crude mixture was purified using normal phase chromatography eluting with a 10-30% methanol/DCM gradient to provide Intermediate 1D as a white solid (5.80 g, 98%).

Workup

  1. stirringthe resulting mixture was stirred under nitrogen for 48 hours
  2. customThe resulting mixture was quenched with water and neutralized with saturated NaHCO3 solution
  3. extractionThe mixture was extracted with DCM
  4. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was purified
  8. washeluting with a 10-30% methanol/DCM gradient

Sources & evidence

ORD record
ord-f3780610f251477baae8da32cba83899
Source dataset
uspto-grants-2009_04
Patent number
US07517874B2

Reaction notes

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