N,N,N',N'-Tetramethylethylenediamine → (1S,2R)-2-(1-Methyl-1H-pyrazol-5-yl)cycloheptanol

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.CN(C)CCN(C)C.C([Li])CCC.[O:20]1[CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:21]12>C1COCC1>[CH3:1][N:2]1[C:6]([C@H:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C@@H:21]2[OH:20])=[CH:5][CH:4]=[N:3]1

Participants

Reactant 4

HCID 8037N,N,N',N'-Tetramethylethylenediamine

HCID 675128-Oxabicyclo(5.1.0)octane

HCID 702551H-Pyrazole, 1-methyl-

HCID 178418339Butyllithium

Product 1

HCID 89963045(1S*,2R*)-2-(1-Methyl-1H-pyrazol-5-yl)cycloheptanolYield 13%

Reagents, catalysts & solvents 1

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 4a by using 1-methylpyrazole (3.66 g, 44.6 mmol), N,N,N′,N′-tetramethylethylenediamine (6.68 mL, 44.6 mmol), n-butyl lithium (1.63 M solution in hexane; 32 mL, 52.2 mmol), 1,2-epoxycycloheptane (5.0 g, 44.6 mmol) and THF (60 mL), to yield the title compound (1.13 g, 13%) as a colorless oil.