Chloromethyl Methyl Ether → HCID 89963013, compound

HRID 338033Notes

Reaction equation

HRID 338033 reaction equation
[NH:1]1[CH:5]=[C:4]([C@@H:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]2[OH:12])[CH:3]=[N:2]1.[CH3:13][O:14][CH2:15]Cl>CN(C=O)C>[CH3:13][O:14][CH2:15][N:1]1[CH:5]=[C:4]([C@@H:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]2[OH:12])[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 89962282HCID 89962282, compound

Product 1

HCID 89963013HCID 89963013, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the (1R,2S)-2-(1H-pyrazol-4-yl)cyclohexanol (170 mg, 1.02 mmol) prepared in Example 169b in DMF (5.0 mL), chloromethyl methyl ether (0.078 mL, 1.02 mmol) was added, and the reaction solution was stirred at room temperature for 2 hours. The reaction solution was vacuum concentrated, and the residue was then purified with silica gel chromatography (hexane/ethyl acetate=7:3) to yield the title compound (132 mg, 61%) as a colorless solid.

Workup

  1. concentrationconcentrated
  2. customthe residue was then purified with silica gel chromatography (hexane/ethyl acetate=7:3)

Sources & evidence

ORD record
ord-4ba879dbb1574a0491c8f5f3d7caa458
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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