Diethyl Ether → HCID 21270415, compound

HRID 649586Notes

Reaction equation

HRID 649586 reaction equation
C(N([CH2:6][CH3:7])CC)C.[N:8]1([C:13]2[CH2:14][N:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH:17]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1.C([CH:24]([C:28](Cl)=[O:29])[C:25](Cl)=[O:26])C.CC[O:33]CC>CN(C)C1C=CN=CC=1>[C:28]([CH2:24][C:25]([C:17]1[CH2:16][N:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][C:13]=1[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:26])([O:29][CH2:6][CH3:7])=[O:33]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 8471TriethylamineHCID 109209242-Ethylpropanedioyl dichlorideHCID 21270429HCID 21270429, compound

Product 1

HCID 21270415HCID 21270415, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Triethylamine (28 ml) and 2,4 g of 4-dimethylaminopyridine are added to a solution of 39.3 g (0.2 moles) of 3-pyrrolidino-N-methoxycarbonyl-2,5-dihydropyrrole in 850 ml of dry ether. The reaction mixture is cooled in an ice bath. A solution of 25.6 ml of ethyl malonyl chloride in 850 ml ether is added dropwise keeping the internal temperature below 5°. After 1 hour at 5° and 2 hours at room temperature, the suspension is filtered, the ether solution is washed with 10% ice cold citric acid and saturated NaHCO3 solution. The organic layer is dried over MgSO4, filtered and evaporated to yield 3-carboethoxyacetyl-4-pyrrolidino-N-methoxycarbonyl-2,5 dihydropyrrole as an oil; NMR (CDCl3) 4.44 (s), 4,37 (s), 4.17 (q) 3,73 (s), 3,42 (m), 3.32 (s), 1.90 (m) and 1.26 (t).

Workup

  1. temperatureThe reaction mixture is cooled in an ice bath
  2. customthe internal temperature below 5°
  3. filtration2 hours at room temperature, the suspension is filtered
  4. washthe ether solution is washed with 10% ice cold citric acid and saturated NaHCO3 solution
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-1e99c99388d145949abbb60419020e40
Source dataset
uspto-grants-1988_04
Patent number
US04740512

Reaction notes

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