2,3-dihydro-1H-pyrrolizine → HCID 13478513, compound

HRID 484740Notes

Reaction equation

HRID 484740 reaction equation
[CH2:1]1[C:8]2[N:4]([CH:5]=[CH:6][CH:7]=2)[CH2:3][CH2:2]1.Cl[C:10]([C:12]1[N:16]([CH3:17])[C:15]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:14][C:13]=1[CH3:23])=[O:11]>C(Cl)Cl>[CH3:17][N:16]1[C:12]([C:10]([C:5]2[N:4]3[C:8](=[CH:7][CH:6]=2)[CH2:1][CH2:2][CH2:3]3)=[O:11])=[C:13]([CH3:23])[CH:14]=[C:15]1[CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

4

Reactant 2

HCID 2593612,3-dihydro-1H-pyrrolizineHCID 13478512HCID 13478512, compound

Product 1

HCID 13478513HCID 13478513, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred, ice-cooled mixture of 2,3-dihydro-1H-pyrrolizine (0.40 g, 0.0037 m), methyl 5-(chlorocarbonyl)-1,4-dimethylpyrrole-2-acetate (1.1 g, 0.0037 m), and methylene chloride (10 ml) was added dropwise over 3 minutes stannic chloride (0.86 ml, 0.0075 m), and the resulting mixture allowed to stir cold for ca. 30 minutes. The mixture was partitioned between ether and water, and the ether layer washed and dried. It was concentrated in vacuo to a yellow residue which was then eluted on a silica gel chromatograph column with 30% ethyl acetate/hexane to yield 0.35 g of methyl 1,4-dimethyl-5-(2,3-dihydro-1H-pyrrolizin-5-oyl)pyrrole-2-acetate.

Workup

  1. temperatureTo a stirred, ice-cooled
  2. customThe mixture was partitioned between ether and water
  3. washthe ether layer washed
  4. customdried
  5. concentrationIt was concentrated in vacuo to a yellow residue which
  6. washwas then eluted on a silica gel chromatograph column with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4dc0728bdc434017871b5dca0eb3a350
Source dataset
uspto-grants-1985_08
Patent number
US04533671

Reaction notes

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