N,N,N',N'-Tetramethylethylenediamine → (1S*,2R*)-2-(1-Ethyl-1H-pyrazol-5-yl)cyclopentanol

HRID 337772Notes

Reaction equation

HRID 337772 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][CH:5]=[N:4]1)[CH3:2].CN(C)CCN(C)C.C([Li])CCC.[CH:21]12[O:26][CH:22]1[CH2:23][CH2:24][CH2:25]2>C1COCC1>[CH2:1]([N:3]1[C:7]([C@H:21]2[CH2:25][CH2:24][CH2:23][C@@H:22]2[OH:26])=[CH:6][CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 4984461-EthylpyrazoleHCID 178418339Butyllithium

Product 1

HCID 89962858(1S*,2R*)-2-(1-Ethyl-1H-pyrazol-5-yl)cyclopentanolYield 16.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 4a by using 1-ethylpyrazole (97%, 2.53 g, 25.5 mmol), N,N,N′,N′-tetramethylethylenediamine (3.83 mL, 25.5 mmol), butyl lithium (1.63 M solution in hexane; 18.3 mL, 29.8 mmol), cyclopentene oxide (2.66 g, 31.6 mmol) and THF (60 mL), to yield the title compound (750 mg, 16%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-05a9bcb18e5f4bd0ade8566e27e5e889
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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