Formaldehyde → (Racemic)-1-[4-(3-Methoxy-1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

HRID 1534554Notes

Reaction equation

HRID 1534554 reaction equation
[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:8]([N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16])[C:9]#[CH:10].[CH2:17]=O.[OH-].[Na+]>O.O1CCOCC1.C(O)(=O)C>[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:17][C:10]#[C:9][CH2:8][N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH2:4]1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 113554473-MethoxypyrrolidineHCID 124643131-(Prop-2-yn-1-yl)pyrrolidin-2-one

Product 1

HCID 15086789(Racemic)-1-[4-(3-Methoxy-1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinoneYield 61%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 365 mg of (racemic)-3-methoxypyrrolidine, 530 mg of N-propargyl-2-pyrrolidinone, 180 mg of paraformaldehyde, 0.6 ml of acetic acid, 20 ml of dioxane and 10 mg of cuprous chloride was stirred at reflux under argon for 1 hour. The reaction was cooled and treated with a mixture of 3 ml of 5N sodium hydroxide and 2 ml of water. The mixture was extracted twice with dichloromethane. The extracts were combined, dried, filtered and concentrated in vacuo to an oil. The oil was purified by chromatography (alumina), giving 520 mg of the desired product as a yellow oil.

Workup

  1. temperatureat reflux under argon for 1 hour
  2. temperatureThe reaction was cooled
  3. extractionThe mixture was extracted twice with dichloromethane
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to an oil
  7. customThe oil was purified by chromatography (alumina)

Sources & evidence

ORD record
ord-2e1a48158c6d4d458e644c6871ece2c0
Source dataset
uspto-grants-1992_02
Patent number
US05089518

Reaction notes

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