[Methoxy(tetrahydro-4H-pyran-4-ylidene)methoxy](trimethyl)silane → Methyl 4-{[4-(2-{[4-(benzyloxy)-1,2-benzisoxazol-3-yl]oxy}ethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate

HRID 2410329Notes

Reaction equation

HRID 2410329 reaction equation
[CH3:1][O:2][C:3](=[C:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[O:4][Si](C)(C)C.[CH2:15]([O:22][C:23]1[C:28]2[C:29]([O:32][CH2:33][CH2:34][CH:35]3[CH2:40][CH2:39][N:38]([CH2:41]OCC)[CH2:37][CH2:36]3)=[N:30][O:31][C:27]=2[CH:26]=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C.[Cl-].[Mg+2].[Cl-]>[CH2:15]([O:22][C:23]1[C:28]2[C:29]([O:32][CH2:33][CH2:34][CH:35]3[CH2:40][CH2:39][N:38]([CH2:41][C:9]4([C:3]([O:2][CH3:1])=[O:4])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]4)[CH2:37][CH2:36]3)=[N:30][O:31][C:27]=2[CH:26]=[CH:25][CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 24897138[Methoxy(tetrahydro-4H-pyran-4-ylidene)methoxy](trimethyl)silaneHCID 693157784-(Benzyloxy)-3-{2-[1-(ethoxymethyl)piperidin-4-yl]ethoxy}-1,2-benzisoxazole

Product 1

HCID 69317575Methyl 4-{[4-(2-{[4-(benzyloxy)-1,2-benzisoxazol-3-yl]oxy}ethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 5360315Magnesium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

[Methoxy(tetrahydro-4H-pyran-4-ylidene)methoxy](trimethyl)silane (2.2 g, 10.0 mmol, EXAMPLE 1, step 3) was added to the mixture of 4-(benzyloxy)-3-{2-[1-(ethoxymethyl)piperidin-4-yl]ethoxy}-1,2-benzisoxazole (3.4 g, 8.4 mmol, EXAMPLE 7, step 4) and magnesium chloride (40 mg, 0.42 mmol) in acetonitrile (16.0 mL) at ambient temperature. After being stirred at room temperature for 3 h, the mixture was concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (ethyl acetate/hexane 2:3) to give 3.2 g (75%) of the title compound as a colorless oil.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give an oil
  3. customThe residual oil was purified by silica gel column chromatography (ethyl acetate/hexane 2:3)

Sources & evidence

ORD record
ord-bb82add5273f4fc090b47f1f769abdac
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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