Benzylamine → HCID 13163461, compound

HRID 1486806Notes

Reaction equation

HRID 1486806 reaction equation
[CH2:1]([CH:3]1[CH2:5][O:4]1)[CH3:2].[CH2:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[CH2:6]([N:13]([CH2:5][CH:3]([OH:4])[CH2:1][CH3:2])[CH2:5][CH:3]([OH:4])[CH2:1][CH3:2])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 78341,2-Epoxybutane

Product 1

HCID 13163461HCID 13163461, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-ethyloxirane, 103 (621 mg, 8.61 mmol, R=ethyl) in DCM (60 mL) was added benzylamine (996 mg, 9.30 mmol) followed by scandium triflate (341 mg, 0.693 mmol) under a nitrogen atmosphere. The reaction mixture was stirred at rt for 20 h after which time the completed reaction was quenched with saturated NaHCO3 (20 mL), extracted three times with DCM (10 mL each), and the combined organic layers was dried over MgSO4, filtered and concentrated to dry. The crude product was purified over silica gel (Biotage 25 g, eluting with a 10:10:0.1 ratio of heptanes:EtOAc:TEA) to provide 1,1′-(benzylazanediyl)bis(butan-2-ol), 104 (658 mg, 2.628 mmol, 30.4% yield, R=ethyl) after concentration of the combined desired fractions and drying in vacuo.

Workup

  1. customthe completed reaction
  2. customwas quenched with saturated NaHCO3 (20 mL)
  3. extractionextracted three times with DCM (10 mL each)
  4. dry with materialthe combined organic layers was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto dry
  8. customThe crude product was purified over silica gel (Biotage 25 g
  9. washeluting with a 10:10:0.1 ratio of heptanes

Sources & evidence

ORD record
ord-cf9fc60ac292477d803d3986621c6e56
Source dataset
uspto-grants-2016_08
Patent number
US09428495B2

Reaction notes

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