Trifluoroacetic acid → 5-Benzyl-2-methyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione

HRID 2043086Notes

Reaction equation

FC(F)(F)C(O)=O.[CH2:8]([N:15]([CH2:21]OC)[CH2:16][Si](C)(C)C)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:24][N:25]1[C:29](=[O:30])[CH:28]=[CH:27][C:26]1=[O:31]>ClCCl>[CH2:8]([N:15]1[CH2:16][CH:27]2[C:26](=[O:31])[N:25]([CH3:24])[C:29](=[O:30])[CH:28]2[CH2:21]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Trifluoroacetic acid (2.4 g) was added dropwise to a solution of benzyl-methoxymethyltrimethylsilanylmethylamine (5.1 g) and 1-methylpyrrole-2,5-dione (2.98 g) in dichloromethane (50 ml) at 0° C. Stirring at 0° C. for 15 minutes was followed by further stirring at room temperature for one hour. The reaction mixture was diluted with dichloromethane, washed with sodium bicarbonate solution and water, dried over magnesium sulfate and concentrated. The product with the molecular weight of 244.30 (C14H16N2O2); MS (ESI): 245 (M+H+) was obtained in this way.

Workup

stirringby further stirring at room temperature for one hour
washwashed with sodium bicarbonate solution and water
dry with materialdried over magnesium sulfate
concentrationconcentrated
customMS (ESI): 245 (M+H+) was obtained in this way

Sources & evidence

ORD record: ord-025d9d5388a14fe4abdccfaef0e1c610
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586609B2

Reaction notes

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