Hydrochloric Acid → HCID 57656224, compound

Participants

Reaction Steps

Dissolve 6-(3,3-dimethyl-butoxy)-nicotinonitrile (1.4 g, 6.86 mmol) in anhydrous THF (10 mL) under nitrogen and add 1M BH3-THF complex in THF (20.6 mL, 20.6 mmol). Stir the mixture overnight under nitrogen and then pour the reaction carefully into 5N aqueous HCl (20 mL). Stir the resulting suspension for 6 h at room temperature. Then basify by adding 2N aqueous NaOH (50 mL) and extract with dichloromethane (3×100 mL). Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Take-up the resulting oil in methanol and filter it through an SCX column eluting with methanol followed by 3M ammonia in methanol. Concentrate in vacuo to obtain the title compound (754 g, 50%). GC-MS m/z: 208 (M>).

Provenance & Evidence