Tetrahydro-4H-pyran-4-one → HCID 57753365, compound

HRID 225631Notes

Reaction equation

HRID 225631 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[O:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1>C1COCC1>[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:26]3([OH:29])[CH2:27][CH2:28][O:23][CH2:24][CH2:25]3)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 534165502-Benzyl-5-bromoisoindolineHCID 178418339Butyllithium

Product 1

HCID 57753365HCID 57753365, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 1.54 mmol 2-benzyl-5-bromo-2,3-dihydro-1H-isoindole in 3 ml THF at −78° C. was added dropwise 3.85 mmol butyllithium solution (1.6 M in hexane) and stirring continued at −78° C. for 1 h. To the resulting yellow solution was added dropwise a solution of 3.08 mmol tetrahydro-4H-pyran-4-one in 0.7 ml THF and the mixture was stirred at −78° C. for 30 min and then allowed to warm to room temperature. The reaction was quenched by addition of 1 M aq HCl, diluted with ethyl acetate, and then made basic by addition of 2 M aq NaOH. The phases were separated and the organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a yellow solid (25% yield). MS (m/e): 310.3 ([M+H]+, 100%).

Workup

  1. stirringthe mixture was stirred at −78° C. for 30 min
  2. customThe reaction was quenched by addition of 1 M aq HCl
  3. additiondiluted with ethyl acetate
  4. additionmade basic by addition of 2 M aq NaOH
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-8da5d520b30a4237a6bba7e6d165a8de
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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