3-Pyrroline → HCID 22393777, compound

HRID 1071640Notes

Reaction equation

HRID 1071640 reaction equation
C(P(=O)(OCC)OCC)#N.[NH:11]1[CH2:15][CH:14]=[CH:13][CH2:12]1.[C:16]([C:18]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)([CH:24]([CH3:26])[CH3:25])[CH2:19][CH2:20][C:21](O)=[O:22])#[N:17]>O1CCCC1>[N:11]1([C:21](=[O:22])[CH2:20][CH2:19][C:18]([CH:24]([CH3:25])[CH3:26])([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[C:16]#[N:17])[CH2:15][CH:14]=[CH:13][CH2:12]1

Participants

5

Reactant 3

HCID 660593-PyrrolineHCID 76257Diethyl cyanophosphonateHCID 22393581HCID 22393581, compound

Product 1

HCID 22393777HCID 22393777, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, diethyl cyanophosphonate (618 mg) was added to a tetrahydrofuran solution (15 ml) of 3-pyrroline (262 mg) and 4-cyano-4-(2-thienyl)-5-methylhexanoic acid (692 mg) at room temperature, and the mixture was stirred overnight. After the reaction solution was evaporated, the crude product was purified by silica gel column chromatography (hexane/ethyl acetate system), to give the title compound as a yellow oil (440 mg).

Workup

  1. customAfter the reaction solution was evaporated
  2. customthe crude product was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-555fe9e250df4d469b5b27f306fad7a9
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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