Hydrochloric Acid → HCID 18324527, compound

HRID 1251876Notes

Reaction equation

HRID 1251876 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:36]=[CH:35][C:7]([C:8]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[CH2:16][O:17][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:9])=[CH:6][CH:5]=1.Cl>CO>[F:3][C:4]1[CH:36]=[CH:35][C:7]([CH:8]([OH:9])[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[CH2:16][O:17][Si:18]([C:31]([CH3:33])([CH3:32])[CH3:34])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18324464HCID 18324464, compound

Product 1

HCID 18324527HCID 18324527, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.41 g; 1.06 mmol) was added portionwise at 0° C. to a solution of 1-(4-fluorobenzoylmethyl)-2-(tert-butyldiphenylsilyloxymethyl)imidazole (4.81 g; 1.01 mmol) in methanol (100 ml). The mixture was stirred at ambient temperature for 16 hours. 12N HCl (0.84 ml) added and then evaporated to dryness and purified by flash column chromatography eluting with dichloromethane/ethanol (96:4) to give 1-[2-(4-fluorophenyl)-2-hydroxyethyl]-2-(tert-butyldiphenylsilyloxymethyl)imidazole.

Workup

  1. customevaporated to dryness
  2. custompurified by flash column chromatography
  3. washeluting with dichloromethane/ethanol (96:4)

Sources & evidence

ORD record
ord-6fe5be608e074bbf8f842dde7aa15bb8
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

Loading…