Formaldehyde → (cis)-2,6-Dimethyl-4-({1-[4-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)morpholine

Participants

Reaction Steps

A solution of (cis)-2,6-dimethylmorpholine (0.111 mL, 0.900 mmol, Alfa Aesar, Ward Hill, USA) and formaldehyde (37%, aqueous, 0.067 mL, 0.9 mmol) in methanol (4 mL) was stirred at room temperature for 1.5 h before adding trimethylsilyl azide (0.155 mL, 1.170 mmol) and 4-(trifluoromethyl)phenyl isocyanide (200 mg, 1.170 mmol). After stirring for 2 days at room temperature, the mixture was filtered and the solid collected was purified by silica gel column chromatography (Biotage SP4, gradient elution: 0-100% EtOAc in iso-hexane) to give the title compound as a solid (241 mg).

Provenance & Evidence