Methanol → HCID 59452515, compound

HRID 1097542Notes

Reaction equation

HRID 1097542 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][OH:5].Br[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]Br)[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>CS(C)=O>[CH3:1][O:2][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][O:5][CH3:4])[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

Participants

5

Reactant 3

HCID 887MethanolHCID 10864974HCID 10864974, compound2×HCID 10942334Sodium Methoxide

Product 1

HCID 59452515HCID 59452515, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

25 wt. % Sodium methoxide in MeOH (3.8 mL, 16 mmol) was added to a suspension of 3a,6a-bis(bromomethyl)-2,5-bis((4-methylphenyl)sulfonyl)octahydropyrrolo[3,4-c]pyrrole (Intermediate 1) (2 g, 3.30 mmol) in DMSO (10 mL) and the mixture was stirred at 120° C. under N2 for 16 h. The solvent was evaporated under vacuum and the residue was partitioned between CHCl3 and sat. NH4Cl (aq). The organic layer was washed with brine, dried (MgSO4) and concentrated to an orange solid, which was triturated with CH2Cl2 to yield the first crop of 3a,6a-bis(methoxymethyl)-2,5-bis((4-methylphenyl)sulfonyl)octahydropyrrolo[3,4-c]pyrrole (720 mg, 1.4 mmol, 43%) as a white solid. The mother liquor was purified by flash silica chromatography (SiO2, eluted with EtOAc/Hexanes 1:2) to yield additional desired product (130 mg, 0.26 mmol, 8%) as awhite solid. LCMS: m/e=509 (M+H)+. LCMS retention time: 1.85 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=2 min. Flow Rate=4 mL/min.).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was partitioned between CHCl3 and sat. NH4Cl (aq)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to an orange solid, which
  6. customwas triturated with CH2Cl2

Sources & evidence

ORD record
ord-dc7b7adb80104dd68700e39f59053d9f
Source dataset
uspto-grants-2012_03
Patent number
US08143244B2

Reaction notes

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