Pentane → HCID 59452543, compound

HRID 1097543Notes

Reaction equation

HRID 1097543 reaction equation
C([Li])(C)(C)C.I[CH2:7][C:8]12[CH2:25][N:24]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH2:23][C:9]1([CH2:36]I)[CH2:10][N:11]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:12]2.CCCCC>C1COCC1>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([N:11]2[CH2:10][C:9]34[CH2:36][CH2:7][C:8]3([CH2:25][N:24]([S:26]([C:29]3[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=3)(=[O:28])=[O:27])[CH2:23]4)[CH2:12]2)(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8003PentaneHCID 59452555HCID 59452555, compoundHCID 178418306HCID 178418306, compound2×

Product 1

HCID 59452543HCID 59452543, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

t-Butyl lithium (1.7 M pentane) (1.05 mL, 1.76 mmol) was added dropwise to a stirring solution of 3a,6a-bis(iodomethyl)-2,5-bis((4-methylphenyl)sulfonyl)octahydropyrrolo[3,4-c]pyrrole (0.50 g, 0.71 mmol) in THF (10 mL) at −78° C. The resulting orange mixture was stirred at −78° C. for 30 minutes. After this time, additional t-Butyl lithium 1.7 M in pentane (1.05 mL, 1.76 mmol) was added to the reaction mixture at −78° C. After 10 minutes of additional stirring at −78° C., the reaction was quenched with the addition of sat. NH4Cl (aq) (10 mL). The mixture was warmed to r.t., diluted with EtOAc (15 mL) and the layers were separated. The aq. layer was then extracted with EtOAc (3×20 mL) and once with CH2Cl2. The combined organic extracts were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated to give 2,5-bis((4-methylphenyl)sulfonyl)tetrahydro-1H,4H-3a,6a-ethanopyrrolo[3,4-c]pyrrole (0.308 g, 0.690 mmol, 97% yield) as a white crystaline solid. LCMS: m/e=447 (M+H)+. LCMS retention time: 2.39 min. (Column: SunFire C18 5u 4.6×50 mm. Solvent A=90% Water/10% Acetonitrile/0.1% TFA. Solvent B=10% Water/90% Acetonitrile/0.1% TFA. Start % B=0. Final % B=100. Gradient Time=3 min. Flow Rate=4 mL/min.). Structure was verified via single crystal X-ray diffraction. 1H NMR (400 MHz, CHLOROFORM-d) □ ppm 7.67 (4 H, d, J=8.28 Hz), 7.34 (4 H, d, J=8.03 Hz), 3.36 (4 H, d, J=9.79 Hz), 2.73 (4 H, d, J=9.79 Hz), 2.47 (6 H, s), 2.00 (4 H, s).

Workup

  1. stirringAfter 10 minutes of additional stirring at −78° C.
  2. customthe reaction was quenched with the addition of sat. NH4Cl (aq) (10 mL)
  3. temperatureThe mixture was warmed to r.t.
  4. additiondiluted with EtOAc (15 mL)
  5. customthe layers were separated
  6. extractionThe aq. layer was then extracted with EtOAc (3×20 mL) and once with CH2Cl2
  7. washThe combined organic extracts were washed with brine (30 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e6a33ff5e71c460cba9fa3a26f34f122
Source dataset
uspto-grants-2012_03
Patent number
US08143244B2

Reaction notes

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