Water → HCID 67773374, compound

Participants

Reaction Conditions

Reaction Steps

To a 1M solution of LAH in THF (31.2 mL, 31.2 mmol) was (S)-tert-butyl 1-(azetidin-1-yl)-1-oxopentan-2-ylcarbamate (Compound E) (2.0 g, 7.80 mmol) dropwise added (over approximately 60 min) as a solution in THF (40 mL) under a nitrogen atmosphere. The resultant mixture was stirred at rt for 30 min and heated at 55° C. over night. The reaction mixture was cooled to 0° C. Water (1.5 mL) was slowly added, followed by THF (10 mL), 15% aq. NaOH (1.5 mL) and additional water (4 mL). The reaction mixture was warmed to rt and stirred for 1 h. The mixture was filtered and the solid was washed with THF. The filtrate was dried (Na2SO4) and concentrated under reduced pressure to give the title compound (1.22 g, quant. yield). The obtained crude product was used without further purification. 1H NMR (400 MHz, CH3OD) δ 0.90, 1.13-1.41, 2.04, 2.23-2.43, 3.08-3.24. Total no of protons: 19. LCMS (M+H)+: 157.

Provenance & Evidence