Benzyl Alcohol → HCID 123524169, compound

Participants

Reaction Conditions

Reaction Steps

A 500 mL three-neck flask was charged with 5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-1-isopropyl-1H-pyrazole-3-carboxylic acid (26 g, 53 mmol), diisopropylethylamine (14 mL, 0.080 mol), benzyl alcohol (17.26 g, 159.6 mmol) and anhydrous toluene (300 mL). The reaction mixture was purged with nitrogen for 2 min and heated to 100° C. Diphenyl phosphorazidate (17.2 mL, 79.85 mmol) was added dropwise to the reaction mixture, and the reaction was maintained at 100° C. After 16 h, the reaction mixture was concentrated in vacuo. The resulting residue was purified by flash column chromatography (20:1 petroleum ether/ethyl acetate) to afford benzyl (5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-1-isopropyl-1H-pyrazol-3-yl)carbamate as a yellow oil (28 g, 89%). LRMS: [M+H]+ 594.0.

Provenance & Evidence