Hydrochloric Acid → 1-(4-Cyano-3-fluorobenzyl)-5-(hydroxymethyl)imidazole

HRID 2306169Notes

Reaction equation

HRID 2306169 reaction equation
C([O:4][CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[C:14]([F:20])[CH:13]=2)[CH:9]=[N:8][CH:7]=1)(=O)C.O.[OH-].[Li+].Cl>C1COCC1.O>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:10]2[C:6]([CH2:5][OH:4])=[CH:7][N:8]=[CH:9]2)=[CH:13][C:14]=1[F:20])#[N:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 184758825-(Acetoxymethyl)-1-(4-cyano-3-fluorobenzyl)imidazole

Product 1

HCID 185360621-(4-Cyano-3-fluorobenzyl)-5-(hydroxymethyl)imidazole

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 5-(acetoxymethyl)-1-(4-cyano-3-fluorobenzyl) imidazole, as described above in Step E, (19.8 g, 72.5 mmol) in 5:1 THF/water (430 mL) at ambient temperature was added lithium hydroxide monohydrate (3.33 g, 79.4 mmol). After 4 hours, the solution was adjusted to pH 7 with 1.0 N hydrochloric acid and concentrated in vacuo. The residue was concentrated from toluene in vacuo (3×100 mL) to give the titled product as a pale solid.

Workup

  1. concentrationconcentrated in vacuo
  2. concentrationThe residue was concentrated from toluene in vacuo (3×100 mL)

Sources & evidence

ORD record
ord-f274d50393d44553959beabb5e6768c2
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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