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

HRID 1090854Notes

Reaction equation

[Mn]([O-])(=O)(=O)=O.[K+].C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].[C:19]([C:27]1[N:28]([CH2:32][CH2:33][CH:34]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:29]=[CH:30][CH:31]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)(=O)C.O.O.O.O.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.O>[C:19]([C:27]1[N:28]2[C:29](=[CH:30][CH:31]=1)[C:34]([C:40]([O:42][CH2:43][CH3:44])=[O:41])([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:33][CH2:32]2)(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a hot (80° C.) solution of manganese(II) acetate tetrahydrate (858 mg, 3.50 mmol) in acetic acid (8 mL) were added sequentially potassium permanganate (138 mg, 0.875 mmol), acetic anhydride (1,355 mg, 10.5 mmol), anhydrous sodium acetate (420 mg, 5 mmol) and a solution of 2-benzoyl-1-[3,3-di(ethoxycarbonyl)propyl]pyrrole (500 mg, 1.40 mmol) in acetic acid (2 mL). The resulting mixture was stirred at 80° C. for 6 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 to provide 478 mg (96%) of diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate (I).

Workup

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-3c6d4ecaf9f84d6d9ec562e69df70706
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05082951

Reaction notes

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