Methanol → HCID 59452515, compound

Participants

Reaction Conditions

Reaction Steps

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.).

Provenance & Evidence