Isopropanol → HCID 178453348, compound

Participants

Reaction Steps

(2-Cyano-ethyl)-carbamic acid tert-butyl ester (59.5 g, 0.35 mol) is dissolved in dry m-xylene 460 ml) and stirred at room temperature. Azidotributyltin (140 g, 0.42 mol) is added and the reaction mixture is heated to 115° C. overnight. On cooling to room temperature, the reaction mixture is quenched with 2M NaOH (500 ml), the layers are separated and the aqueous phase is acidified with 6M HCl to pH 2 resulting in a thick precipitate. DCM (500 ml) is added followed by IPA (50 ml) resulting in clear layers, the organic layer is separated and the aqueous is re-extracted with 9:1 DCM/IPA (2×250 ml). The organic layers are combined, washed with brine (500 ml), dried over MgSO4, filtered and concentrated in vacuo. The resulting solid is triturated with iso-hexanes (250 ml), stirred for 1 hour at room temperature then a further 1 hour at 5-10° C., filtered and dried under vacuum to afford the title compound.

Provenance & Evidence