1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 23138791, compound

HRID 1171707Notes

Reaction equation

HRID 1171707 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:11](/[CH:12]=[C:13]2\[CH2:14][N:15]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:17][CH:18]\2O)=[CH:10][N:9]=[CH:8]1)=[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].C(SC1CCN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C/C/1=C\C1N(CC(OCC)=O)C=NC=1)(=O)C>CN(C)C=O>[C:55]([S:57][CH:12]([C:11]1[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:8]=[N:9][CH:10]=1)[C:13]1[CH2:14][N:15]([C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:16][CH2:17][CH:18]=1)(=[O:58])[CH3:56]

Participants

6

Reactant 4

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23138491HCID 23138491, compoundHCID 23138897HCID 23138897, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 23138791HCID 23138791, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-{[1-(ethoxycarbonylmethyl)-1H-imidazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (560 mg) in N,N-dimethylformamide (5 ml) were added N,N-dimethylformamide dineopentyl acetal (2.5 ml) and thioacetic acid (0.6 ml) at room temperature. After being stirred at the same temperature for 1.5 hour, the mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Solvents were removed under reduced pressure, and residue was purified by silica gel chromatography using hexane, ethyl acetate, and dichloromethane (1:2:2) as an eluent. In a separate run, further starting material (E)-3-{[1-(ethoxycarbonylmethyl)-1H-imidazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (1.0 g) was subjected to the similar reaction/purification procedure. Both products were combined to afford an approximately 5:2 mixture of (E)-4-(acetylsulfanyl)-3-{[1-(ethoxycarbonylmethyl)-1H-imidazol-5-yl]methylidene}-1-(triphenylmethyl)piperidine and 5-{(acetylsulfanyl)[1-(ethoxycarbonylmethyl)-1H-imidazol-5-yl]methyl}-1-(triphenylmethyl)-1,2,3,6-tetrahydropyridine (500 mg, gross yield: 29%), as a yellow amorphous solid.

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSolvents were removed under reduced pressure, and residue
  6. customwas purified by silica gel chromatography
  7. customwas subjected to the similar reaction/purification procedure
  8. customto afford

Sources & evidence

ORD record
ord-90e7ae607caa4be4b2eb6505a1d0278a
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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