Water → HCID 67773219, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-tert-butyl 1-(azetidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (Compound D) (20 g, 78 mmol) in THF (200 mL) was dropwise charged (over approximately 90 min) to a jacketed reactor containing a 1M solution of LAH in THF (200 mL, 200 mmol) under a nitrogen atmosphere. The resultant mixture was heated at 60° C. over night. The reaction was cooled to −5° C. and H2O (7.6 mL) was slowly added. The mixture was diluted with THF (200 mL). A 15% aq. NaOH (7.6 mL) solution and additional H2O (22.8 mL) were added. The mixture was warmed to 25° C. and stirred for 1 h. The slurry was filtered and solids were washed with THF. The filtrate was concentrated under reduced pressure to give the title compound (1.7 g, 79%). The obtained crude product was used without further purification. 1H NMR (400 MHz, CH3OD) δ 0.86, 1.75-1.90, 1.94-2.18, 2.18-2.36, 2.38, 2.99-3.29. Total no of protons: 19.

Provenance & Evidence