Tetrahydrofuran → 1-(3,3,3-Trifluoro-2-(methylamino)propyl)azetidin-3-ol

Tert-butyl 1,1,1-trifluoro-3-(3-hydroxyazetidin-1-yl)-3-oxopropan-2-ylcarbamate (Compound B3.1) (3.97 gg, 13.3 mmol) was added under argon in portions to 1M solution of LAH in THF (53 mL, 53 mmol) over 15 min. The mixture was heated under argon to reflux for 7 h. After additional standing for 15 h at rt EtOAc (10 mL) was added dropwise under ice cooling, followed by addition of water/THF (1:1, 12 mL). The mixture was diluted with DCM (120 mL). Celite was added and the suspension was stirred for 10 min. The mixture was filtered, the solids washed with DCM (2×50 mL). The combined filtrates were dried (Na2SO4) and concentrated under reduced pressure to give the title compound (2.39 g, 91%). The obtained crude product was used in the next step without characterization.

1. temperatureThe mixture was heated under argon
2. temperatureto reflux for 7 h
3. additionCelite was added
4. filtrationThe mixture was filtered
5. washthe solids washed with DCM (2×50 mL)
6. dry with materialThe combined filtrates were dried (Na2SO4)
7. concentrationconcentrated under reduced pressure

ORD record

ord-7dabb5b3159f4ad5a1c6519a5740c9b1

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08361998B2