1,2-Diaminocyclohexane, trans- → HCID 86722431, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottom flask equipped with an air cooled reflux container was charged with 5,7,8,9-tetrahydro-1H-spiro[cyclohepta[f]indazole-6,2′-[1,3]dioxolane] (81) (3.00 g, 12.3 mmol), 4-iodo-2-methylpyridine (3.84 g, 14.7 mmol), CuI (0.234 g, 1.23 mmol), (+/−)-trans-cyclohexane-1,2-diamine (0.295 mL, 2.46 mmol) and K3PO4 (5.21 g, 24.6 mmol) in 1,4-dioxane (31 mL). The reaction mixture was heated at about 100° C. for about 21 h. The reaction was allowed to cool and then it was filtered through a pad of Celite® and rinsed with EtOAc (3×10 mL). The filtrate was concentrated then the residue was purified on silica gel (120 g), using a gradient of 10-100% EtOAc in DCM). Collection and concentration of the appropriate fractions gave 1-(2-methylpyridin-4-yl)-5,7,8,9-tetrahydro-1H-spiro[cyclohepta[f]indazole-6,2′-[1,3]dioxolane] (82, R1=2-methylpyridin-4-yl) (3.26 g, 79%); LC/MS, method 3, Rt=1.86 min, MS m/z 336 (M+H)+.

Provenance & Evidence