Pyridine → HCID 24277608, compound

HRID 1908691Notes

Reaction equation

HRID 1908691 reaction equation
[C:1]12([CH2:15][C:14](=O)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7]1)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2.Cl.O([NH2:20])C.N1C=CC=CC=1>CO.Cl>[C:1]12([CH2:15][CH:14]([NH2:20])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7]1)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 11106781Spiro[chroman-2,1'-cyclohexan]-4-one

Product 1

HCID 24277608HCID 24277608, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of the product from Example 1A (3.022 g, 13.99 mmol) in methanol (50 mL) was added methoxylamine hydrochloride (1.17 g, 14.0 mmol) and pyridine (5.7 mL, 70.5 mmol). The mixture was stirred overnight at room temperature and was then evaporated in vacuo. The residue was partitioned between ethyl acetate and H2O, and the organic layer was dried over Na2SO4, filtered and evaporated in vacuo. The residue thus obtained was dissolved in methanol (50 mL) and was hydrogenated (balloon) over 10% Pd-on-carbon in the presence of 4 drops of conc. HCl overnight at room temperature. After this time, the catalyst was filtered off (Celite), and the filtrate was evaporated in vacuo. The residue was taken up in ether (50 mL) and was extracted with 1N HCl (3×20 mL). These acidic extracts were then basified to pH 10 with 2N NaOH and were extracted with ethyl acetate (3×20 mL). The organic extracts were dried over Na2SO4, filtered and evaporated in vacuo to yield the title compound as a yellow oil, 880 mg (29%). 1H NMR (300 MHz, DMSO-d6) δ ppm 7.52 (m, 1H), 7.06 (m, 1H), 6.82 (td; J=7.4, 1.3 Hz; 1H), 6.69 (dd; J=8.1, 1.3 Hz; 1H), 3.83 (dd; J=11.1, 6.3 Hz; 1H), 2.08 (dd; J=13.5, 6.3 Hz; 1H), 1.90 (m, 1H), 1.74 (m, 2H), 1.31-1.57 (m, 8H); MS (ESI) m/z 218 (M+H).

Workup

  1. customwas then evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and H2O
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue thus obtained
  7. customat room temperature
  8. filtrationAfter this time, the catalyst was filtered off (Celite)
  9. customthe filtrate was evaporated in vacuo
  10. extractionwas extracted with 1N HCl (3×20 mL)
  11. extractionwere extracted with ethyl acetate (3×20 mL)
  12. dry with materialThe organic extracts were dried over Na2SO4
  13. filtrationfiltered
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-8757a1ba3db04be7b601f9192f60a1e4
Source dataset
uspto-grants-2013_12
Patent number
US08598220B2

Reaction notes

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