Aluminium lithium hydride → 1-Benzyl-5,5-dimethylpyrrolidin-3-amine

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of (3E)-5,5-dimethyl-1-(phenylmethyl)-2,3-pyrrolidinedione 3-(O-methyloxime) (4.2872 g, 17.41 mmol) in THF (90 mL) was added LiAlH4 (2.64 g, 69.57 mmol) portionwise. The mixture was heated at 70° C. and stirred for 6.5 h. The mixture was then cooled to room temperature and quenched by addition of Na2SO4.10H2O (3 g), followed by 1 N aq. NaOH (100 mL). The mixture was extracted with Et2O (2×150 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was diluted with DCM (200 mL), and the mixture was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give crude racemic 5,5-dimethyl-1-(phenylmethyl)-3-pyrrolidinamine (3.2293 g, 86%) as a light yellow oil. LCMS: (M+H)+: 205.2.

Provenance & Evidence