Acetic Acid → HCID 11489769, compound

HRID 1820292Notes

Reaction equation

HRID 1820292 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=O)=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:31][CH2:32][CH2:33][C:34]1([CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][CH:45]([N:48]([C:56]3[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][CH:57]=3)[C:49]([C:51]3[O:52][CH:53]=[CH:54][CH:55]=3)=[O:50])[CH2:44][CH2:43]2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>ClCCCl.C(Cl)(Cl)Cl>[O:7]=[C:5]1[C:4]2[C:3](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:1][N:31]1[CH2:32][CH2:33][C:34]1([CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][CH:45]([N:48]([C:56]3[CH:57]=[CH:58][C:59]([CH3:62])=[CH:60][CH:61]=3)[C:49]([C:51]3[O:52][CH:53]=[CH:54][CH:55]=3)=[O:50])[CH2:44][CH2:43]2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 243003Methyl 2-formylbenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 23109894HCID 23109894, compound

Product 1

HCID 11489769HCID 11489769, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

After adding methyl 2-formylbenzoate (254 mg, 1.55 mmol), acetic acid (89 μL, 1.55 mmol) and sodium triacetoxyborohydride (265 mg, 1.25 mmol) to a solution of N-[1-[2-[1-(2-aminoethyl)cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (226 mg, 0.52 mmol) in 1,2-dichloroethane (3 mL), the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with chloroform and washed with saturated aqueous sodium hydrogencarbonate and saturated brine in that order. The organic layer was dried (anhydrous sodium sulfate) and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (10 g NH Silica Chromatorex DM2035, hexane:ethyl acetate=7:3-1:1) to obtain the title compound as a colorless oil (194 mg, 0.26 mmol) (67% yield).

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate and saturated brine in that order
  2. dry with materialThe organic layer was dried (anhydrous sodium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (10 g NH Silica Chromatorex DM2035, hexane:ethyl acetate=7:3-1:1)

Sources & evidence

ORD record
ord-21e8721aafc647d0bf1d32e2ed5f2898
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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