Water → HCID 67773742, compound

Temperature

70 °C

To a 1M solution of LAH in THF (22.26 mL, 22.26 mmol) was (S)-tert-butyl 1-(4-methoxypiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (Compound I1) (1.75 g, 5.57 mmol) dropwise added (over approximately 60 min) as a solution in THF (20 mL) under a nitrogen atmosphere. The resultant mixture was stirred at rt for 30 min and heated at 70° C. over night. The reaction was cooled to 0° C. Water (1 mL) was slowly added, followed by 15% aq. NaOH (1 mL), THF (20 mL) and additional water (2 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 (0.95 g, 80%). The obtained crude product was used without further purification. 1H NMR (400 MHz, CH3OD) δ 0.90, 1.44-1.69, 1.74-1.98, 1.98-2.12, 2.32, 2.53-2.71, 2.71-2.93, 3.15-3.29, 3.30. LCMS (M+H)+: 215.

1. temperatureThe reaction 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-c75271a538aa4ca9bf1db9c5a902742d

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08361998B2