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

HRID 1090856Notes

Reaction equation

HRID 1090856 reaction equation
[C:1]([C:9]1[NH:10][CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15][C:16](Br)([C:22]([O:24]CC)=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(B([CH2:33][CH3:34])CC)C.O>C1C=CC=CC=1>[C:1]([C:9]1[N:10]2[C:15](=[CH:14][CH:13]=1)[C:16]([C:22]([O:24][CH2:33][CH3:34])=[O:23])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][CH2:11]2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7357Triethylborane2×HCID 53682870HCID 53682870, compound

Product 1

HCID 9928574diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2-benzoyl-[3-bromo-3,3-di(ethoxycarbonyl)propyl]pyrrole (436 mg, 1.0 mmol) in benzene (20 mL) was added triethylborane (1.0M in hexane, 5 mL, 5 mmol). The reaction mixture was stirred in an open vessel for one hour. Additional triethylborane (1 mL, 1 mmol) was added and the reaction was allowed to stir in an open vessel for an additional hour. The reaction mixture was poured into water and extracted with diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate (85:15) to provide 266 mg (75%) of diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate.

Workup

  1. stirringto stir in an open vessel for an additional hour
  2. extractionextracted with diethyl ether
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate (85:15)

Sources & evidence

ORD record
ord-01d23d37945e4afaa583ab780fffc225
Source dataset
uspto-grants-1992_01
Patent number
US05082951

Reaction notes

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