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

HRID 1734236Notes

Reaction equation

HRID 1734236 reaction equation
O=P(Cl)(Cl)Cl.[C:6](N1CCOCC1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:20]([O:22][C:23]([C:25]1([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:32]2[N:28]([CH:29]=[CH:30][CH:31]=2)[CH2:27][CH2:26]1)=[O:24])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C>[C:6]([C:29]1[N:28]2[C:32](=[CH:31][CH:30]=1)[C:25]([C:33]([O:35][CH2:36][CH3:37])=[O:34])([C:23]([O:22][CH2:20][CH3:21])=[O:24])[CH2:26][CH2:27]2)(=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 15114Morpholine, 4-benzoyl-HCID 24813Phosphorus oxychlorideHCID 10705887HCID 10705887, compound

Product 1

HCID 9928574diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylateYield 100.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of POCl3 (166 mg, 1.08 mmole) and N-benzoylmorpholine (96 mg, 0.5 mmole) was maintain for 6 hours at 25° C. A solution of diethyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate (126 mg, 05 mmole) in dichloroethane (2 ml) was added. Then, the mixture was maintained at 50° C. for 3 days. The reacted mixture was poured with 2.5 ml of 10% aqueous sodium carbonate solution. The mixture was stirred at room temperature for 10 hours, and refluxed for 2 hours. The organic layer was separated, and the aqueous layer was washed with 1,2-dichloroethane. The organic layer was dried using sodium carbonate, and the solvent was removed. Finally, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (1:9) as an eluting solvent and 178 mg of the product diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate (84%) was obtained. The IR and NMR spectral properties were identical to those of an authentic sample.

Workup

  1. temperatureThen, the mixture was maintained at 50° C. for 3 days
  2. temperaturerefluxed for 2 hours
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed with 1,2-dichloroethane
  5. customThe organic layer was dried
  6. customthe solvent was removed
  7. customFinally, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-930d8b62fece46b993f84ede156603d2
Source dataset
uspto-grants-1996_07
Patent number
US05532381

Reaction notes

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