Triethylamine → HCID 131727787, compound

HRID 1438110Notes

Reaction equation

HRID 1438110 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)/[CH:7]=[N:8]/[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])([O-:3])=[O:2].C(N(CC)CC)C>ClCCl.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[N+:1]([C:4]1[CH:5]=[C:6]([C@H:7]2[C@@H:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][CH2:9][NH:8]2)[CH:16]=[CH:17][CH:18]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 178500504HCID 178500504, compound

Product 1

HCID 131727787HCID 131727787, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 160960Diamminetetrachlorotitanate(IV)CatalystHCID 6344DichloromethaneSolvent

Procedure

To the imine 15A (1.0 g, 2.84 mmol) and triethylamine (0.39 mL, 2.84 mmol) in dichloromethane (50 mL) at −10° C. was added titanium chloride (11.3 mL, 1.0 M in dichloromethane) dropwise under argon. The reaction was stirred at rt for 4 h and then quenched with saturated potassium carbonate. The mixture was filtered through celite and the aqueous layer was extracted with dichloromethane (2×). The organic extracts were combined, washed with brine and dried over sodium sulfate. The solvent was evaporated and the crude residue was purified by preparative HPLC equipped with a YMC ODS S5 (30×100 mm) column. The separation was performed using a linear gradient (solvent A: 10% acetonitrile-90% water-0.1% TFA; solvent B: 90% acetonitrile-90% water-0.1% TFA; 0 to 100% B in 12 min with a flow rate of 40 mL/min to give 0.32 g of 15B as a solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 2.53 (m, 2H) 3.47 (s, 3H) 3.62 (m, 1H) 3.79 (m, 2H) 5.14 (d, J=6.85 Hz, 1H) 7.76 (m, 2H) 8.33 (m, 2H).

Workup

  1. customquenched with saturated potassium carbonate
  2. filtrationThe mixture was filtered through celite
  3. extractionthe aqueous layer was extracted with dichloromethane (2×)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated
  7. customthe crude residue was purified by preparative HPLC
  8. customequipped with a YMC ODS
  9. customThe separation

Sources & evidence

ORD record
ord-df71303e6da6436180d3934bb5b66995
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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