HCID 123524169, compound → HCID 131735792, compound

Participants

Reaction Steps

To a solution of benzyl (5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-1-isopropyl-1H-pyrazol-3-yl)carbamate (28 g, 47 mmol) in methanol (200 mL) was added 10% palladium on carbon (2.8 g). The reaction mixture was stirred at room temperature under 1 atm of hydrogen. After 16 h, the reaction mixture was filtered through Celite. The filtrate was concentrated in vacuo to provide crude 5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-1-isopropyl-1H-pyrazol-3-amine which was dissolved in acetonitrile (200 mL). A solution of 4-methylbenzenesulfonic acid monohydrate (22.34 g, 117.5 mmol) in water (25 mL) was added at room temperature. After 30 min at room temperature, the reaction mixture was cooled to 0° C. A solution of sodium nitrite (5.4 g, 78 mmol) and sodium iodide (1174 g, 78.31 mmol) in water (25 mL) was added dropwise to the reaction mixture.

Provenance & Evidence