4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 58103852, compound

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Reaction Steps

A mixture of 4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexanone (1.72 ml, 6.85 mml) [C.A.S.55145-45-4], 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (1 g, 4.56 mmol) and sodium triacetoxy-borohydride (1.44 g, 6.85 mmol) in DCM (25 ml) was stirred at r.t. for 1 day. Then, the mixture was washed with NH4Cl (aqueous sat. solution). The organic layer was collected, dried (MgSO4) and evaporated in vacuo. The crude product thus obtained was purified by column chromatography (silica gel; heptane/EtOAc up to 5% as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate compound D32-a (trans) (0.566 g, 31%) and D32-b (cis) (1.089 g, 61%).

Provenance & Evidence