N,N,N',N'-Tetramethylethylenediamine → HCID 89963110, compound

HRID 337888Notes

Reaction equation

HRID 337888 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:6]=1.CN(C)CCN(C)C.C([Li])(C)(C)C.[F:26][C:27]1([F:34])[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]1>C1COCC1>[F:26][C:27]1([F:34])[CH2:32][CH2:31][C:30]([C:2]2[CH:3]=[N:4][N:5]([CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][O:8]3)[CH:6]=2)([OH:33])[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 157890924,4-DifluorocyclohexanoneHCID 162167094-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 89963110HCID 89963110, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 4a by using 4-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (J. Org. Chem., 2007, 72 (9), 3589-3591; 10.0 g, 35.9 mmol), N,N,N′,N′-tetramethylethylenediamine (5.38 mL, 35.9 mmol), t-butyl lithium (1.60 M solution in pentane; 26.2 mL, 43.2 mmol), 4,4-difluorocyclohexanone (4.82 g, 35.9 mmol) and THF (100 mL), to yield the title compound (1.10 g, 11%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-9e8d028c4501494685c4000c39550d8f
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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