Triethylamine → HCID 23510337, compound

HRID 1883198Notes

Reaction equation

HRID 1883198 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6]C(S(O)(=O)=O)=[CH:4][CH:3]=1.Cl.O.[NH:15]1[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1.[BH-](O[C:32]([CH3:34])=[O:33])(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+].[CH2:41]([N:43](CC)[CH2:44][CH3:45])[CH3:42]>CC(C)=O.ClCCCl.O>[NH:43]1[CH:44]=[CH:45][CH:42]=[C:41]1[C:32]([C:34]1[CH:4]=[CH:3][C:2]([CH2:12][N:15]2[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]2)=[CH:7][CH:6]=1)=[O:33]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 2723901PiperonylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23510337HCID 23510337, compoundYield 81.8%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
56 °C

Procedure

To a solution of the compound of Example 163-2 (300 mg) in acetone (30 mL) were added water (3 mL) and p-toluenesulfonic acid monohydrate (66 mg), and the mixture was stirred at 56° C. for 1.5 hour. The solvent was evaporated under reduced pressure, and thereto was added a NaHCO3 solution, and the mixture was extracted twice with ethyl acetate-toluene, and dried over MgSO4. The solvent was evaporated under reduced pressure to give crude (4-formylphenyl)(1H-pyrrol-2-yl)methanone (258 mg). To a solution of this compound (170 mg) in 1,2-dichloroethane (20 mL) were added successively 4-piperidone monohydrate hydrochloride (263 mg), triethylamine (261 mg) and NaBH(OAc)3 (546 mg), and the mixture was stirred at room temperature for 71 hours. To the mixture was added NaHCO3, and the mixture was extracted twice with ethyl acetate, and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=2/1→1/1) to give 1-[4-(1H-pyrrol-2-ylcarbonyl)benzyl]piperidin-4-one (80.1 mg, 33%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionwas added a NaHCO3 solution
  3. extractionthe mixture was extracted twice with ethyl acetate-toluene
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated under reduced pressure
  6. customto give crude (4-formylphenyl)(1H-pyrrol-2-yl)methanone (258 mg)
  7. stirringthe mixture was stirred at room temperature for 71 hours
  8. extractionthe mixture was extracted twice with ethyl acetate
  9. dry with materialdried over MgSO4
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by silica gel column (hexane/ethyl acetate=2/1→1/1)

Sources & evidence

ORD record
ord-3efd2205e38840b78c9b3c62cfef19a0
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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