Thionyl Chloride → HCID 59533567, compound

Participants

Reaction Steps

To a solution of ((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridine-8-yl)methanol (1) (2.5 g, 7.1 mmol) in chloroform (35 mL) was added thionyl chloride (1.3 mL, 18 mmol). The resulting mixture was heated at reflux for 4-8 hours until reaction was judged complete by TLC (98:2 CH2Cl2/2-PrOH). Solvent and excess reagent were evaporated in vacuo and the residue was chromatographed (98:2 CH2Cl2/2-PrOH) to give the title compound (2.2 g, 85%). Product was characterized via HPLC/MS (MH+=369). Purity was judged as >95%.

Provenance & Evidence