HCID 13424017, compound → HCID 13490406, compound

HRID 485368Notes

Reaction equation

HRID 485368 reaction equation
[CH3:1][C:2]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]2[N:4]([CH2:5][CH2:6][CH:7]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:3]=1.[CH2:20]1[C:27]2[N:23]([C:24]([C:28](Cl)=[O:29])=[CH:25][CH:26]=2)[CH2:22][CH2:21]1>C(Cl)Cl>[CH2:20]1[C:27]2[N:23]([C:24]([C:28]([C:3]3[N:4]4[C:8](=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]=3[CH3:1])[CH:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:6][CH2:5]4)=[O:29])=[CH:25][CH:26]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 13424017HCID 13424017, compoundHCID 134904052,3-Dihydro-1H-pyrrolizine-5-carbonyl chloride

Product 1

HCID 13490406HCID 13490406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-bath cooled solution of diethyl 6-methyl-2,3-dihydro-1H-pyrrolizine-1,7-dicarboxylate (2.0 g, 0.0075 m) in methylene chloride (25 ml) was added stannic chloride (2.6 ml, 0.0225 m) all at once. A solution of 2,3-dihydro-1H-pyrrolizine-5-carbonyl chloride (1.1 g, 0.0075 m) in methylene chloride (10 ml) was then added dropwise, and the resultant mixture stirred cold for two hours, then at ambient temperatures overnight. The reaction mixture was then quenched with excess ice-H2O and ether, the organic layer removed, washed well with water, dried over sodium sulfate, filtered, and concentrated in vacuo to a residue. Trituration with either yielded 1.75 g of diethyl 5-(2,3-dihydro-1H-pyrrolizin-5-oyl)-6-methyl-2,3-dihydro-1H-pyrrolizine-1,7-dicarboxylate as a white solid.

Workup

  1. customat ambient temperatures overnight
  2. customThe reaction mixture was then quenched with excess ice-H2O and ether
  3. customthe organic layer removed
  4. washwashed well with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a residue

Sources & evidence

ORD record
ord-b71273306cbc4184829032b36600f215
Source dataset
uspto-grants-1985_08
Patent number
US04536512

Reaction notes

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