Formaldehyde → (S)-1-[4-[3-(Acetyloxy)-1-pyrrolidinyl]-2-butynyl]-2-pyrrolidinone

HRID 1534547Notes

Reaction equation

HRID 1534547 reaction equation
[C:1]([O:4][C@H:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)(=[O:3])[CH3:2].[CH2:10]([N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18])[C:11]#[CH:12].[CH2:19]=O>O1CCOCC1>[C:1]([O:4][C@H:5]1[CH2:9][CH2:8][N:7]([CH2:19][C:12]#[C:11][CH2:10][N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 124643131-(Prop-2-yn-1-yl)pyrrolidin-2-oneHCID 15046661acetic acid (S)-pyrrolidin-3-yl ester

Product 1

HCID 15046674(S)-1-[4-[3-(Acetyloxy)-1-pyrrolidinyl]-2-butynyl]-2-pyrrolidinoneYield 47.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 500 mg of (S)-3-acetoxypyrrolidine, 530 mg of N-propargyl-2-pyrrolidinone, 150 mg of paraformaldehyde and 50 mg of cupric chloride in 10 ml of dioxane was stirred at reflux under argon for 4 hours. The dioxane was evaporated, the residue was treated with 5 ml of 1N hydrochloric acid and extracted twice with ether. The aqueous acid was basified with 1 g of sodium bicarbonate and extracted twice with dichloromethane. The extracts were combined, dried, filtered and concentrated in vacuo to an oil. This oil was purified by chromatography (alumina), giving 490 mg of the desired product as a yellow oil, [α]D26 =-3° (c, 1.02, methanol).

Workup

  1. temperatureat reflux under argon for 4 hours
  2. customThe dioxane was evaporated
  3. additionthe residue was treated with 5 ml of 1N hydrochloric acid
  4. extractionextracted twice with ether
  5. extractionextracted twice with dichloromethane
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to an oil
  9. customThis oil was purified by chromatography (alumina)

Sources & evidence

ORD record
ord-6d78fea1436244f9b0d1de8c1f12463a
Source dataset
uspto-grants-1992_02
Patent number
US05089518

Reaction notes

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