HCID 53436965, compound → HCID 54162915, compound

HRID 704449Notes

Reaction equation

HRID 704449 reaction equation
[C:1]([C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4]OC)#[N:2].[N:11]1([CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14][CH2:13][CH2:12]1>O1CCCC1>[C:1]([C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:17]1[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)#[N:2]

Participants

4

Reactant 2

HCID 53436965HCID 53436965, compoundHCID 538895841-(Hex-1-en-1-yl)pyrrolidine

Product 1

HCID 54162915HCID 54162915, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Cyano-2methoxy-1-methoxycarbonyl-ethene (8.5 g, 0.06 mol) in tetrahydrofuran (60 ml) was chilled to -25° C. At this temperature, a solution of 1-pyrrolidino-hexene (9.1 g, 0.06 mol) in tetrahydrofuran (30 ml) was added dropwise. Cooling was then stopped and the reaction mixture was allowed to warm up to room temperature. The solution was then stirred for 1 hour and then evaporated. The resulting gum was triturated with isopropanol and the resulting solid material collected by vacuum filtration. After drying, yellowish crystals of 1-cyano-1-methoxycarbonyl-2-(2-pyrrolidino-cyclohexenyl)-ethene (9.5 g, 60.9% of theoretical yield; m.pt. 133° C.-134° C.) Were obtained. The compound migrated in tlc uniformly and was used for the next step without further purification.

Workup

  1. temperatureCooling
  2. customevaporated
  3. customThe resulting gum was triturated with isopropanol
  4. filtrationthe resulting solid material collected by vacuum filtration
  5. customAfter drying

Sources & evidence

ORD record
ord-85e594fe76cf457e86899314bde16c14
Source dataset
uspto-grants-1991_01
Patent number
US04987232

Reaction notes

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