Sodium Hydroxide → tert-Butyl 2-(aminomethyl)-7-azaspiro[3.5]nonane-7-carboxylate

Participants

Reaction Steps

To a solution of 1.40 g (5.59 mmol) of tert-butyl 2-cyano-7-azaspiro[3.5]nonane-7-carboxylate (Chem. Pharm. Bull.; 52 (6), 675-687, 2004), in 10 mL of a 1N solution of sodium hydroxide in ethanol. 0.164 g (2.80 mmol) of Raney nickel is then added. The reaction medium is placed in a Parr flask under a hydrogen atmosphere (60 psi) at room temperature for 2 hours. The resulting mixture is filtered through a Büchner funnel and the filtrate is then concentrated under reduced pressure. Dichloromethane is added, the aqueous phase is separated out and extracted three times with dichloromethane, and the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate. After evaporating off the solvent, 1.212 g of product are obtained in the form of a colourless oil, which is used without further purification in the following step.

Provenance & Evidence