1,4-Dioxane → HCID 117970160, compound

HRID 2271314Notes

Reaction equation

HRID 2271314 reaction equation
[CH3:1][C:2]1[C:6](=[O:7])[O:5][C@H:4]([O:8]/[CH:9]=[C:10]2\[C@H:11]3[CH2:18][CH:17]=[CH:16][C@H:12]3[NH:13][C:14]\2=[O:15])[CH:3]=1.[O:19]1CCOCC1>>[OH:19][C@H:18]1[C@H:11]2[C@H:12]([NH:13][C:14](=[O:15])/[C:10]/2=[CH:9]/[O:8][C@@H:4]2[CH:3]=[C:2]([CH3:1])[C:6](=[O:7])[O:5]2)[CH:16]=[CH:17]1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 129172249HCID 129172249, compound

Product 1

HCID 117970160HCID 117970160, compoundYield 44%

Conditions

Temperature
100 °C

Procedure

To a solution of (3E,3aR,6aR)-3-[[(2S)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylene]-1,3a,4,6a-tetrahydrocyclopenta[b]pyrrol-2-one Ia-1″ (125 mg, 0.50 mmol) in 1,4-dioxane (2.5 mL) was added SeO2 (67.1 mg, 0.60 mmol) The suspension was stirred at 100° C. for 4 h then the dark suspension was then allowed to cool to room temperature followed by filtration and concentration under reduced pressure. Purification using flash chromatography (CH2Cl2/MeOH, gradient) afforded the desired compound as a dark oil (58 mg, 44%); 1H NMR (400 MHz, MeOH-d4) 7.35 (1H, d), 7.16 (1H, m), 6.38 (1H, m), 5.95 (1H, dd), 5.91 (1H, m), 4.76 (1H, m), 4.72 (1H, m), 3.39 (1H, m), 1.97 (3H, m): LCMS (Method D): 0.24 min; ES+264 (M+H+).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfollowed by filtration and concentration under reduced pressure
  3. customPurification

Sources & evidence

ORD record
ord-8bb4272a2b9a49ddb14df29155111070
Source dataset
uspto-grants-2015_09
Patent number
US09119398B2

Reaction notes

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