Hydrochloric Acid → HCID 15284546, compound

HRID 964039Notes

Reaction equation

HRID 964039 reaction equation
[CH3:1][C:2]1([CH3:20])[C:6]2(OCC[O:7]2)[CH2:5][N:4]([C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:3]1=[O:19].Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:20][C:2]1([CH3:1])[C:6](=[O:7])[CH2:5][N:4]([C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:3]1=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acid2×HCID 15284545HCID 15284545, compound

Product 1

HCID 15284546HCID 15284546, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 18.23 g of 9,9-dimethyl-8-oxo-7-[1-(R)-phenylethyl]-7-aza-1,4-dioxaspiro[4.4]nonane, 70 ml of 1N hydrochloric acid and 20 g of p-toluenesulfonic acid in 250 ml of acetone was heated under reflux for 20 hrs. During the reaction, 20 g of p-toluenesulfonic acid was further added. Solvent was removed under reduced pressure and the residue was extracted with chloroform. The extract was washed with a saturated sodium bicarbonate aqueous solution and dried. Solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography (300 g of silica gel in a column) while eluting with a mixture of n-hexane and ethyl acetate (4:1, v/v) to yield 11.85 g of the titled compound. 1H-NM(CDCl3) δ ppm;1.20, 1.26 (each 3H, s), 1.60 (2H, ABq, J=16 Hz), 5.80 (1H, q, J=7.2 Hz), 7.32 (5H, s)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hrs
  3. additionwas further added
  4. customSolvent was removed under reduced pressure
  5. extractionthe residue was extracted with chloroform
  6. washThe extract was washed with a saturated sodium bicarbonate aqueous solution
  7. customdried
  8. customSolvent was removed under reduced pressure
  9. customthe residue was purified by silica gel chromatography (300 g of silica gel in a column)
  10. washwhile eluting with a mixture of n-hexane and ethyl acetate (4:1

Sources & evidence

ORD record
ord-957c731330244bb28b8f8b50aa92cbf1
Source dataset
uspto-grants-1998_06
Patent number
US05767127

Reaction notes

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