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

HRID 2107981노트

반응식

HRID 2107981 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-53b2e45541cf46e1967bdf520c71b437
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04937235

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