1H-Pyrazole, 1-methyl- → HCID 89962272, compound

HRID 337908Notes

Reaction equation

HRID 337908 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.C([Li])CCC.[CH2:12]([O:19][C@@H:20]1[CH2:26][CH2:25][C@H:24]2[C@H:22]([O:23]2)[CH2:21]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:12]([O:19][C@@H:20]1[CH2:26][CH2:25][C@H:24]([OH:23])[C@@H:22]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[CH2:21]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 702551H-Pyrazole, 1-methyl-HCID 12827120HCID 12827120, compoundHCID 178418339Butyllithium

Product 1

HCID 89962272HCID 89962272, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 4a by using 1-methylpyrazole (650 mg, 7.92 mmol), n-butyl lithium (2.69 M solution in hexane; 3.08 mL, 8.28 mmol), (1R*,3R*,6S*)-3-(benzyloxy)-7-oxabicyclo[4.1.0]heptane (Bioorg. Med. Chem. 2004, 12, 1459; 1.54 g, 7.54 mmol) and THF (45 mL), to yield the title compound (790 mg, 37%) as a colorless solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-76306a6d24734d9b8f7ac6f2683af088
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

Loading…