Synthesis of 3-deuterated diazepam and nordiazepam 4-oxides and their use in the synthesis of other 3-deuterated derivatives

Article abstract of DOI:10.1002/(SICI)1099-1344(199608)38:8<753::AID-JLCR890>3.0.CO;2-N

The protons at 3-positions of diazepam 4-oxide and nordiazepam 4-oxide underwent an efficient deuterium exchange via keto-enol tautomerism in deuterated alkaline methanol. The 3-dideuterated 4-oxides were each used as a starting material to synthesize 3-monodeuterated oxazepam and its 3-acetate, 3-monodeuterated temazepam and its 3-acetate, and 3-dideuterated diazepam and nordiazepam.