Hydrochloric Acid → HCID 59271874, compound

The 6-methyltetrahydro-2H-pyran-2-ol (42 g, 350 mmol) was dissolved in dioxane (300 mL) and treated with methylamine (40% in water, 32 mL, 350 mmol) followed by methylamine.HCl (19 g, 280 mmol) and then sodium cyanide (17 g, 350 mmol) followed by water (50 mL). After stirring at room temperature overnight, the organic phase was decanted off and concentrated. The residue was dissolved in ethyl acetate. Water was added to the initial aqueous suspension (which had been left behind) until dissolution was complete, after which both phases were combined and extracted. The organic phase thus obtained was concentrated. The aqueous phase was extracted twice more with fresh ethyl acetate and the extracts concentrated. The combined residue was dissolved in ether and filtered to remove the remaining solids. Concentration gave the product as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 3.81 (m, 1H), 3.46 (t, J=7 Hz, 1H), 2.53 (s, 3H), 1.76 (m, 2H), 1.34-1.65 (m, 4H), 1.19 (d, J=6.2 Hz, 3H).

1. customthe organic phase was decanted off
2. concentrationconcentrated
3. dissolutionThe residue was dissolved in ethyl acetate
4. additionWater was added to the initial
5. waitaqueous suspension (which had been left behind)
6. dissolutionuntil dissolution
7. extractionextracted
8. customThe organic phase thus obtained
9. concentrationwas concentrated
10. extractionThe aqueous phase was extracted twice more with fresh ethyl acetate
11. concentrationthe extracts concentrated
12. dissolutionThe combined residue was dissolved in ether
13. filtrationfiltered
14. customto remove the remaining solids
15. concentrationConcentration

ORD record

ord-92da444dbf8447409292f5cab6de5ad3

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513234B2