2'-Hydroxyacetophenone → HCID 58551494, compound

HRID 1908019Notes

Reaction equation

HRID 1908019 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].N1CCCC1.[C:16]([C:20]1[CH:34]=[CH:33][C:23]([C:24]([N:26]2[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]2)=[O:25])=[CH:22][C:21]=1[O:35][CH3:36])([CH3:19])([CH3:18])[CH3:17]>CO>[C:16]([C:20]1[CH:34]=[CH:33][C:23]([C:24]([N:26]2[CH2:31][CH2:30][C:29]3([CH2:9][C:8](=[O:10])[C:3]4[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=4)[O:1]3)[CH2:28][CH2:27]2)=[O:25])=[CH:22][C:21]=1[O:35][CH3:36])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 83752'-HydroxyacetophenoneHCID 31268PyrrolidineHCID 58551528HCID 58551528, compound

Product 1

HCID 58551494HCID 58551494, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(2-Hydroxyphenyl)ethanone (260 μL, 2.2 mmol) was added portion-wise at room temperature to pyrrolidine (370 μL, 4.4 mmol) followed by portion-wise addition of 1-(4-tert-butyl-3-methoxy-benzoyl)piperidin-4-one (630 mg, 2.2 mmol). Anhydrous methanol (140 μL) was added and the slurry was heated at 80° C. for 3 h. The mixture was then partitioned between ethyl acetate and 1M aqueous HCl. The layers were separated and the aqueous layer was discarded. Saturated aqueous sodium bicarbonate was added and the layers were separated. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (0-25% ethyl acetate/hexanes) to give 1′-(4-tert-butyl-3-methoxybenzoyl)spiro[chroman-2,4′-piperidin]-4-one (840 mg, 94%) as a light yellow solid. ESI-MS m/z calc. 407.2. found 408.2 (M+1)+; Retention time: 2.07 minutes (3 min run).

Workup

  1. customThe mixture was then partitioned between ethyl acetate and 1M aqueous HCl
  2. customThe layers were separated
  3. additionSaturated aqueous sodium bicarbonate was added
  4. customthe layers were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (0-25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-89814141a42a48d298512f8b2ce26e6b
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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