Lithium aluminum hydride → HCID 58394484, compound

A solution of 1-ethyl-3,3-difluoro-piperidin-4-one oxime (6.186 g, 34.72 mmol) in tetrahydrofuran (300 ml) was cooled to 0° C. over an ice bath and charged with 1M lithium tetrahydroaluminate in tetrahydrofuran (69.4 ml, 69.4 mmol) and left to stand overnight gradually warming to room temperature. The reaction was quenched with the addition of 1 N aqueous solution of sodium potassium tartrate (70 ml) and left to stir for an additional night. The white slurry was extracted twice with ethyl acetate (50 ml) and twice with dichloromethane (50 ml) and dried over sodium sulfate and concentrated under vacuum to yield 4.71 g 1-ethyl-3,3-difluoro-piperidin-4-ylamine (83%) LCMS (Method F): RT=0.14 min, m+H=179.0 1H NMR (400 MHz, D2O) δ 4.07-3.82 (m, 2H), 3.53 (s, 2H), 3.38 (q, J=7.3 Hz, 2H), 3.13 (s, 2H), 1.38 (t, J=7.3 Hz, 3H).

1. waitleft
2. customThe reaction was quenched with the addition of 1 N aqueous solution of sodium potassium tartrate (70 ml)
3. waitleft
4. extractionThe white slurry was extracted twice with ethyl acetate (50 ml) and twice with dichloromethane (50 ml)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under vacuum

ORD record

ord-31d46d30197d430993612436311e4255

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461328B2