Water → 1-((2S,3S)-3-Methyl-2-(methylamino)pentyl)azetidin-3-ol

Participants

Reaction Steps

To LAH (1 M solution in THF) (69.8 mL, 69.84 mmol) was added a solution of tert-butyl (2S,3S)-1-(3-hydroxyazetidin-1-yl)-3-methyl-1-oxopentan-2-ylcarbamate (Compound F2.1) (5 g, 17.5 mmol) in anhydrous THF (24 mL) dropwise (1 h) under nitrogen. The reaction mixture was stirred at rt for 1 h and then heated at 60° C. over night. The reaction mixture was cooled to 0° C. Water (3.5 ml) was added dropwise, followed by 15% aq. NaOH (3.5 ml), THF (50 ml) and water (7.5 ml). The mixture was allowed to reach rt and stirred for 30 min. The solids were filtered off and washed with THF. The filtrate was dried over Na2SO4 and concentrated under reduced pressure to give the title compound as colorless oil (2.8 g, 86%). The product was used in the next step without further purification. 1H NMR (600 MHz, CDCl3) δ 0.80 (d, 3H), 0.91 (t, 3H), 1.10-1.23 (m, 1H), 1.25-1.38 (m, 1H), 1.53-1.63 (m, 1H), 2.15-2.30 (m, 3H), 2.36 (s, 3H), 2.38-2.47 (m, 2H), 2.77-2.84 (m, 1H), 2.89-2.97 (m, 1H), 3.50-3.64 (m, 2H), 4.33-4.44 (m, 1H).

Provenance & Evidence