Trifluoromethanesulfonic anhydride → 5-Acetoxymethyl-1-[2-(1-adamantyl)ethyl]2-n-butylimidazole

A mixture of 2-(1-adamantyl)ethanol (10.7 g) and diisopropylethylamine (11 ml) in methylene chloride (70 ml) was added to triflic anhydride (16.75 g) in 70 ml of methylene chloride at -78° C. for 45 minutes, 1-acetyl-2-n-butyl 5-acetoxymethyl imidazole in 50 ml of methylene chloride was added and the mixture was allowed to stand at room temperature for 4 days, then concentrated and heated on a steam bath with 10% sodium hydroxide (250 ml), diluted with 300 ml of water, extracted with methylene chloride, dried, filtered and concentrated to give an oil. Chromatography on silica gel in methanol/chloroform gave 5-acetoxymethyl-1-[2-(1-adamantyl)-ethyl]-2-n-butyl-imidazole. This acetoxy compound (5.4 g) was stirred at room temperature with potassium hydroxide (5.2 g) in ethanol (200 ml) for one hour, the mixture was concentrated, poured into water, stirred, and filtered to give 1-[2-(1-adamantyl)ethyl]-2-n-butyl-5-hydroxymethyl- 1H-imidazole.

1. concentrationconcentrated
2. temperatureheated on a steam bath with 10% sodium hydroxide (250 ml)
3. additiondiluted with 300 ml of water
4. extractionextracted with methylene chloride
5. customdried
6. filtrationfiltered
7. concentrationconcentrated
8. customto give an oil

ORD record

ord-4abdcb5f4ce64f6f9dc993a5b72d5eb7

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05248689