Acetic Anhydride → diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate

HRID 1090855Notes

Reaction equation

C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[C:25]([C:33]1[N:34]([CH2:38][CH2:39][CH:40]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:35]=[CH:36][CH:37]=1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)(=O)C.O.O.O.O.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.[N+]([O-])([O-])=O.[Ag+].O>[C:25]([C:33]1[N:34]2[C:35](=[CH:36][CH:37]=1)[C:40]([C:46]([O:48][CH2:49][CH3:50])=[O:47])([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:39][CH2:38]2)(=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of manganese(II) acetate tetrahydrate (343 mg, 1.40 mmol), silver nitrate (23.8 mg, 0.140 mmol), sodium acetate (420 mg, 5 mmol), acetic anhydride (542 mg, 4.20 mmol) and sodium persulfate (333 mg, 1.4 mmol) in acetic acid (8 mL) was stirred at 80° C. for 30 minutes. To this mixture was added a solution of 2-benzoyl-1-[3,3-di(ethoxycarbonyl)propyl]pyrrole (500 mg, 1.40 mmol) in acetic acid (2 mL). To the reaction mixture was then added additional sodium persulfate (333 mg, 1.4 mmol). The resulting mixture was stirred at 80° C. for 12 hours, cooled, poured into water (25 mL), and extracted with toluene (3×25 mL). The combined toluene extracts were washed with water (25 mL) and concentrated under reduced pressure, providing 475 mg (95%) of diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate.

Workup

stirringThe resulting mixture was stirred at 80° C. for 12 hours
temperaturecooled
extractionextracted with toluene (3×25 mL)
washThe combined toluene extracts were washed with water (25 mL)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ed9ccb72c04b45c982da079b1f207cdb
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05082951

Reaction notes

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