Triethylamine → HCID 57904800, compound

Temperature

23 °C

To ((2S,6R)-6-cyanotetrahydro-2H-pyran-2-yl)methyl acetate (3.90 g, 21.29 mmol) in methanol (300 mL) was added Et3N (30 mL). The reaction mixture was stirred at 23° C. for 18 h. The solvents were evaporated in vacuo. The residue was redissolved in methanol the solvent removed in vacuo (2×20 mL). The crude material was then purified on a silica gel column (Biotage flash chromatography system) eluting with a gradient mixture ethyl acetate (100%) to ethyl acetate:methanol (8:2) to afford 2.20 g (73% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 4.31 (1 H, dd, J=11.6, 2.5 Hz), 3.58-3.63 (2 H, m), 3.51-3.57 (1 H, m), 2.06 (1 H, s), 1.94-2.03 (2 H, m), 1.79-1.90 (1 H, m), 1.53-1.65 (2 H, m), 1.36-1.47 (1 H, m).

1. customThe solvents were evaporated in vacuo
2. dissolutionThe residue was redissolved in methanol the solvent
3. customremoved in vacuo (2×20 mL)
4. customThe crude material was then purified on a silica gel column (Biotage flash chromatography system)
5. washeluting with a gradient mixture ethyl acetate (100%) to ethyl acetate:methanol (8:2)

ORD record

ord-216218a4bba7446c8940183375234582

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129398B2