(1S)-1-[2-(trifluoromethyl)phenyl]ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a similar manner as described for example B31, 7.3 g of methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-hydroxythiophene-2-carboxylate, 5.0 g of (1S)-1-[2-(trifluoromethyl)phenyl]ethanol, 9.2 g of triphenylphosphine (polymer bound, ˜3 mmol/g) and 8.1 g of di-tert-butyl azodicarboxylate in 180 ml anhydrous dichloromethane yield the title compound.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a nitrogen atmosphere, 4.45 g of methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-hydroxythiophene-2-carboxylate and 3.02 g of (1S)-1-[2-(trifluoromethyl)phenyl]ethanol are dissolved in 140 ml anhydrous dichloromethane. 7.07 g triphenylphosphine (polymer bound, ˜3 mmol/g) and 4.88 g of di-tert-butyl azodicarboxylate are added. The reaction mixture is stirred at room temperature for 90 minutes and then filtered. The filter cake is washed with 10 ml dichloromethane and 10 ml methanol. The filtrate is concentrated to dryness under reduced pressure. filtered The filter cake is washed with 10 ml dichloromethane and 10 ml methanol The filtrate is concentrated to dryness under reduced pressure