1-(Triphenylphosphoranylidene)acetone → 1-(N-Cbz-2-pyrrolidinyl)-1-buten-3-one

HRID 440096

反応式

HRID 440096 の反応式
[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH:13]=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:25][C:26](=[O:28])[CH3:27])C=CC=CC=1>C1C=CC=CC=1>[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][CH:12]1[CH:13]=[CH:25][C:26](=[O:28])[CH3:27])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

参加物

4

反応物 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 11746545(S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

生成物 1

HCID 572702461-(N-Cbz-2-pyrrolidinyl)-1-buten-3-one収率 69%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a stirred solution of N-Cbz-L-prolinal (6.3 g, 27 mmol, from step 24d above) in 30 mL of benzene was added 9.42 g (29.6 mmol) of 1-triphenylphosphoranylidene-2-propanone (Aldrich) at room temperature. The reaction mixture was heated to reflux for 4 hr. The benzene was removed under vacuum, and the residue was dissolved in ether and cooled for 16 hr. The phosphine oxide by product was removed by filtration, and the solution was further purified by column chromatography on silica gel, eluting with 20% ethyl acetate in hexanes, to afford 4.4 g of the title product (69% yield).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hr
  3. customThe benzene was removed under vacuum
  4. dissolutionthe residue was dissolved in ether
  5. temperaturecooled for 16 hr
  6. customThe phosphine oxide by product was removed by filtration
  7. customthe solution was further purified by column chromatography on silica gel
  8. washeluting with 20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-fd7d853d1ad9403c8c3b1b2c8e4ceed7
出典データセット
uspto-grants-1996_05
特許番号
US05516912

関連ノート

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