Sodium Hydroxide → (S)-1-(Azetidin-1-yl)-3-methylbutan-2-amine

Participants

Reaction Conditions

Reaction Steps

To a 1M solution of LAH in THF (19.2 mL, 19.2 mmol) was (S)-2-amino-1-(azetidin-1-yl)-3-methylbutan-1-one (Compound T) (2 g, 12.8 mmol) in THF (12.8 mL) added (over approximately 30 min) at 0° C. under a nitrogen atmosphere. The resultant mixture was stirred at rt for 1 h and heated at 60° C. for 6 h. The reaction was cooled to 0° C. Water (0.73 mL) was slowly added, followed by 15% aq. NaOH (0.73 mL) and additional water (2.2 mL). The reaction mixture was warmed to rt and stirred for 1 h. Celite and Na2SO4 were added. The mixture was filtered and the filtrate concentrated under reduced pressure to give the title compound (1.14 g, 63%). 1H NMR (400 MHz, CDCl3) δ 3.29-3.04, 2.51-2.39, 2.37-2.21, 2.14-1.96, 1.60-1.47, 1.34, 0.94-0.76. Total no of protons: 18.

Provenance & Evidence