Sodium Acetate → diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate

HRID 1090853Notes

Reaction equation

[C:1]([C:9]1[N:10]([CH2:14][CH2:15][CH:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C.C(OCC)C.O.O.C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C>[C:1]([C:9]1[N:10]2[C:11](=[CH:12][CH:13]=1)[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][CH2:14]2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-benzoyl-1-[3,3-di(ethoxycarbonyl)propyl]pyrrole (1.00 g, 2.80 mmol) and anhydrous sodium acetate (4.60 mg, 5.6 mmol) in acetic acid (20 mL) is added manganese(III) acetate dihydrate (2.25 g, 8.4 mmol) The mixture was stirred for two hours at 80° C. The reaction mixture was diluted with diethyl ether (100 mL), and filtered. The resulting solution was washed with water (2×25 mL), 10% sodium hydroxide (2×30 mL), and water (2×25 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude oil was purified by flash chromatography on silica eluting with hexane/ethyl acetate (90:10-80:20) to yield 800 mg (80%) of diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate.

Workup

filtrationfiltered
washThe resulting solution was washed with water (2×25 mL), 10% sodium hydroxide (2×30 mL), and water (2×25 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe crude oil was purified by flash chromatography on silica eluting with hexane/ethyl acetate (90:10-80:20)

Sources & evidence

ORD record: ord-b6f3627e78c44f49889fad260e1e1491
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05082951

Reaction notes

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