Sodium Hydroxide → HCID 67773433, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-tert-butyl 2-(azetidin-1-yl)-1-cyclopropyl-2-oxoethylcarbamate (Compound B1) (1.4 g, 5.50 mmol) in THF (40 mL) was a 1M solution of LAH in THF (16 mL, 16.0 mmol) dropwise added (over approximately 10 min) at −20° C. under a nitrogen atmosphere. The resultant mixture was stirred at rt for 1 h and heated at 60° C. over night. The reaction was cooled to −5° C. and Na2SO4×10H2O (ca 5 g) and NaOH (2M, 2 mL) was added. The mixture was diluted with EtOH (100 mL) and the resultant mixture was warmed to rt and stirred for 1 h. The mixture was filtered and the solid was washed with THF. The filtrate was concentrated under reduced pressure to give the title compound (0.31 g, 37%). The obtained crude product was used without further purification. 1H NMR (400 MHz, CDCl3) δ 0.03, 0.26, 0.33-0.46, 0.50-0.64, 1.51, 2.00-2.12, 2.42-2.48, 2.49, 2.56, 3.19. Total no of protons: 17. LCMS (M+H)+: 155.

Provenance & Evidence