Water → HCID 7154286, compound

Temperature

55 °C

To a 1M solution of LAH in THF (28.1 mL, 28.1 mmol) was (S)-tert-butyl 3,3-dimethyl-1-oxo-1-(pyrrolidin-1-yl)butan-2-ylcarbamate (Compound F1) (2.0 g, 7.03 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 (1.24 g, 96%). The obtained crude product was used without further purification. 1H NMR (400 MHz, CDCl3) δ 0.90, 1.72-1.81, 2.08, 2.26, 2.32-2.48, 2.50, 2.53-2.68. Total no of protons: 23. LCMS (M+H)+: 185.

1. temperatureThe reaction mixture was cooled to 0° C
2. temperatureThe reaction mixture was warmed to rt
3. filtrationThe mixture was filtered
4. washthe solid was washed with THF
5. dry with materialThe filtrate was dried (Na2SO4)
6. concentrationconcentrated under reduced pressure

ORD record

ord-dc7270c153824f8fa3c792984c828c18

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08361998B2