1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 23139094, compound

HRID 1171725Notes

Reaction equation

HRID 1171725 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1/[CH:12]=[C:13]1\[CH2:14][N:15]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:17][CH:18]\1O)=[O:5])[CH3:2].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[C:55]([OH:58])(=[S:57])[CH3:56]>C1(C)C=CC=CC=1>[C:55]([S:57][CH:12]([C:8]1[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=[CH:10][N:9]=1)[C:13]1[CH2:14][N:15]([C:20]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:16][CH2:17][CH:18]=1)(=[O:58])[CH3:56]

Participants

5

Reactant 3

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23139200HCID 23139200, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 23139094HCID 23139094, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (E)-3-{[1-(ethoxycarbonylmethyl)-1H-imidazol-2-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (4.52 g) in toluene (80 ml) were added N,N-dimethylformamide dineopentyl acetal (5.0 ml) and thioacetic acid (1.3 ml) at 0° C. After the mixture was stirred at room temperature, the reaction was quenched by addition of water. The product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure followed by purification of the residue by silica gel chromatography using ethyl acetate and hexane (25:75 to 70:30) gave 5-{(acetylsulfanyl)[1-(ethoxycarbonylmethyl)-1H-imidazol-2-yl]methyl}-1-(triphenylmethyl)-1,2,3,6-tetrahydropyridine (3.92 g, yield: 78%) as a pale yellow amorphous solid.

Workup

  1. customthe reaction was quenched by addition of water
  2. extractionThe product was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. customfollowed by purification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-3be28ddf5fe943e999fb6c2198dad625
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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