Ammonium Chloride → tert-butyl N-methyl-N-(4,4,4trifluoro-3-hydroxybutyl)carbamate

Participants

Reaction Conditions

Reaction Steps

Methyl-(3-oxopropyl)carbamic acid, 1,1-dimethylethyl ester (320 mg, 1.71 mmol) and (trifluoromethyl)trimethylsilane (298 mg, 2.10 mmol) were dissolved in tetrahydrofuran (10 ml) under nitrogen and cooled to 0° C. with stirring. To the resulting solution was added tetrabutylammonium fluoride (1.0M solution in tetrahydrofuran, 1.0 ml, 1.0 mmol) and the mixture was then allowed to warm to room temperature with stirring over 20 h. The mixture was then poured into saturated ammonium chloride solution and then extracted with diethyl ether three times. The combined organic fractions were then washed with brine and dried over magnesium sulphate. The solvent was evaporated and the residue eluted down a flash chromatography column using 50% diethyl ether/isohexane as eluent to give 290 mg (66%) of the title compound as an oil.

Provenance & Evidence