Dimethyl Sulfoxide → 3-Benzyl-3-azabicyclo[3.1.0]hexane-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.88 ml, 17.73 mmol) was added to a stirred flask of DCM (100 ml) under N2 and the solution cooled to an internal temperature of −65° C. DMSO (1.26 ml, 17.73 mmol) was then added dropwise, keeping the internal temperature at −65° C. or below at all times. A solution of (3-benzyl-3-azabicyclo[3.1.0]hex-6-yl)methanol (2.00 g, 9.85 mmol) in DCM (50 ml) was then added to the reaction mixture slowly, again making sure the internal temperature did not rise above −65° C. After this addition was complete, triethylamine (5.90 ml, 42.35 mmol) was slowly added to the reaction, again making sure the internal temperature did not rise above −65° C. After addition was complete the reaction was allowed to warm up to r.t. and solvent removed in vacuo. The residue was purified by column chromatography (25% EtOAc in heptane) to give the title compound as a light yellow oil (1.49 g, 76%). LCMS purity 90%, m/z 202 [M+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 2.11 (2H, m), 2.44 (1H, m), 2.50 (2H, d, J=9.3 Hz), 3.07 (2H, d, J=9.3 Hz), 3.64 (2H, s), 7.21-7.35 (5H, m), 9.31 (1H, d, J=4.8 Hz).

Provenance & Evidence