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

HRID 2107981ノート

反応式

HRID 2107981 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-53b2e45541cf46e1967bdf520c71b437
出典データセット
uspto-grants-1990_06
特許番号
US04937235

反応ノート

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