Sodium borohydride → 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(2-hydroxypropyl)-4-isopropyl-1H-imidazole

HRID 1857709Notes

Reaction equation

HRID 1857709 reaction equation
[C:1]([CH2:4][N:5]1[C:9]([S:10][C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=2)=[C:8]([CH:19]([CH3:21])[CH3:20])[N:7]=[C:6]1[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[CH2:24]([O:23][CH2:22][C:6]1[N:5]([CH2:4][CH:1]([OH:3])[CH3:2])[C:9]([S:10][C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=2)=[C:8]([CH:19]([CH3:21])[CH3:20])[N:7]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:1]([CH2:4][N:5]1[C:9]([S:10][C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[CH:12]=2)=[C:8]([CH:19]([CH3:21])[CH3:20])[N:7]=[C:6]1[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 221309871-acetylmethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole

Product 2

HCID 221303532-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(2-hydroxypropyl)-4-isopropyl-1H-imidazoleHCID 221309871-acetylmethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (5 ml) was dissolved 371 mg (0.8 mmol) of 1-acetylmethyl-2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (17v"), followed by addition of 38 mg (1.0 mmol) of sodium borohydride with stirring at room temperature, and the mixture was stirred for 1.5 hours. This reaction mixture was concentrated under reduced pressure, and to the residue were added water and methylene chloride to extract. The organic layer was washed with water and was dried over sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:methylene chloride=1:9), to obtain 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(2-hydroxypropyl)-4-isopropyl-1H-imidazole (17v'") as oil quantitativelty.

Workup

  1. stirringthe mixture was stirred for 1.5 hours
  2. concentrationThis reaction mixture was concentrated under reduced pressure
  3. additionto the residue were added water and methylene chloride
  4. extractionto extract
  5. washThe organic layer was washed with water
  6. dry with materialwas dried over sodium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (ethyl acetate:methylene chloride=1:9)

Sources & evidence

ORD record
ord-e4f551553633444f88200c19612a662a
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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